PL206026B1 - Sposób wytwarzania pochodnych 4-bromoaniliny - Google Patents
Sposób wytwarzania pochodnych 4-bromoanilinyInfo
- Publication number
- PL206026B1 PL206026B1 PL359155A PL35915501A PL206026B1 PL 206026 B1 PL206026 B1 PL 206026B1 PL 359155 A PL359155 A PL 359155A PL 35915501 A PL35915501 A PL 35915501A PL 206026 B1 PL206026 B1 PL 206026B1
- Authority
- PL
- Poland
- Prior art keywords
- pyridine
- dihydroisoxazol
- methylaniline
- bromo
- hours
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- -1 C1-C6-halogenalkyl Chemical group 0.000 claims abstract description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 35
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 31
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 31
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 14
- ICMSGNRMZFNBLN-UHFFFAOYSA-N 4-bromo-2-(4,5-dihydro-1,2-oxazol-3-yl)-3-methylaniline Chemical compound CC1=C(Br)C=CC(N)=C1C1=NOCC1 ICMSGNRMZFNBLN-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000011877 solvent mixture Substances 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- WDFQBORIUYODSI-IDEBNGHGSA-N 4-bromoaniline Chemical class N[13C]1=[13CH][13CH]=[13C](Br)[13CH]=[13CH]1 WDFQBORIUYODSI-IDEBNGHGSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 13
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000012043 crude product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 5
- HFWVJEXKJBOUHJ-UHFFFAOYSA-N 2-(4,5-dihydro-1,2-oxazol-3-yl)-3-methylaniline Chemical compound CC1=CC=CC(N)=C1C1=NOCC1 HFWVJEXKJBOUHJ-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- AQXNGHALTDOVHV-UHFFFAOYSA-N 4,6-dibromo-2-(4,5-dihydro-1,2-oxazol-3-yl)-3-methylaniline Chemical compound CC1=C(Br)C=C(Br)C(N)=C1C1=NOCC1 AQXNGHALTDOVHV-UHFFFAOYSA-N 0.000 description 3
- XENJLTGXGVSVRN-UHFFFAOYSA-N 6-bromo-2-(4,5-dihydro-1,2-oxazol-3-yl)-3-methylaniline Chemical compound CC1=CC=C(Br)C(N)=C1C1=NOCC1 XENJLTGXGVSVRN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003971 isoxazolinyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- WTTDTHJJRJDEED-UHFFFAOYSA-N 4-bromo-2-(4,5-dihydro-1,2-oxazol-3-yl)-3-ethylaniline Chemical compound CCC1=C(Br)C=CC(N)=C1C1=NOCC1 WTTDTHJJRJDEED-UHFFFAOYSA-N 0.000 description 1
- DUXHISYKBAFUFL-UHFFFAOYSA-N 4-bromo-3-ethyl-2-(1,2-oxazol-3-yl)aniline Chemical compound CCC1=C(Br)C=CC(N)=C1C1=NOC=C1 DUXHISYKBAFUFL-UHFFFAOYSA-N 0.000 description 1
- QKKRSDODWKWWOZ-UHFFFAOYSA-N 4-bromo-3-ethyl-2-(3-methyl-4,5-dihydro-1,2-oxazol-5-yl)aniline Chemical compound CCC1=C(Br)C=CC(N)=C1C1ON=C(C)C1 QKKRSDODWKWWOZ-UHFFFAOYSA-N 0.000 description 1
- ATANWMLVMVFXRM-UHFFFAOYSA-N 4-bromo-3-ethyl-2-(5-methyl-1,2-oxazol-3-yl)aniline Chemical compound CCC1=C(Br)C=CC(N)=C1C1=NOC(C)=C1 ATANWMLVMVFXRM-UHFFFAOYSA-N 0.000 description 1
- RLLNFGRGUBPTLH-UHFFFAOYSA-N 4-bromo-3-methyl-2-(1,2-oxazol-3-yl)aniline Chemical compound CC1=C(Br)C=CC(N)=C1C1=NOC=C1 RLLNFGRGUBPTLH-UHFFFAOYSA-N 0.000 description 1
- YTDUTXAVCVNGBT-UHFFFAOYSA-N 4-bromo-3-methyl-2-(3-methyl-4,5-dihydro-1,2-oxazol-5-yl)aniline Chemical compound C1C(C)=NOC1C1=C(N)C=CC(Br)=C1C YTDUTXAVCVNGBT-UHFFFAOYSA-N 0.000 description 1
- ZSUKUVJCRQGJGV-UHFFFAOYSA-N 4-bromo-3-methyl-2-(5-methyl-1,2-oxazol-3-yl)aniline Chemical compound O1C(C)=CC(C=2C(=C(Br)C=CC=2N)C)=N1 ZSUKUVJCRQGJGV-UHFFFAOYSA-N 0.000 description 1
- NFJSIWUQYGVKTE-UHFFFAOYSA-N 6-amino-3-bromo-2-methylbenzonitrile Chemical compound CC1=C(Br)C=CC(N)=C1C#N NFJSIWUQYGVKTE-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XXSLZJZUSYNITM-UHFFFAOYSA-N tetrabutylammonium tribromide Chemical compound Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC XXSLZJZUSYNITM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10030975 | 2000-06-30 | ||
| PCT/EP2001/007482 WO2002002537A1 (de) | 2000-06-30 | 2001-06-29 | Verfahren zur herstellung von 4-brom-anilin-derivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL359155A1 PL359155A1 (en) | 2004-08-23 |
| PL206026B1 true PL206026B1 (pl) | 2010-06-30 |
Family
ID=7646770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL359155A PL206026B1 (pl) | 2000-06-30 | 2001-06-29 | Sposób wytwarzania pochodnych 4-bromoaniliny |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1296965B1 (enExample) |
| JP (1) | JP4937485B2 (enExample) |
| KR (1) | KR100779315B1 (enExample) |
| CN (1) | CN1182124C (enExample) |
| AT (1) | ATE305928T1 (enExample) |
| AU (2) | AU6911101A (enExample) |
| BR (1) | BRPI0112121B1 (enExample) |
| CA (1) | CA2413723C (enExample) |
| CZ (1) | CZ301413B6 (enExample) |
| DE (1) | DE50107619D1 (enExample) |
| DK (1) | DK1296965T3 (enExample) |
| EA (1) | EA006293B1 (enExample) |
| ES (1) | ES2250425T3 (enExample) |
| HU (1) | HUP0301741A3 (enExample) |
| IL (2) | IL153412A0 (enExample) |
| MX (1) | MXPA02012483A (enExample) |
| NO (1) | NO324408B1 (enExample) |
| NZ (1) | NZ523825A (enExample) |
| PL (1) | PL206026B1 (enExample) |
| SK (1) | SK285627B6 (enExample) |
| WO (1) | WO2002002537A1 (enExample) |
| ZA (1) | ZA200300816B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101516471B1 (ko) * | 2010-05-19 | 2015-05-04 | 로디아 오퍼레이션스 | 오르쏘-치환 5-할로페놀 및 이의 합성 중간체의 제조 방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6377844A (ja) * | 1986-09-18 | 1988-04-08 | Nippon Kayaku Co Ltd | ｐ−ブロモアニリン類の製造法 |
| JPH0816085B2 (ja) * | 1988-06-07 | 1996-02-21 | 日本化薬株式会社 | ２−ブロモ−４−フルオロアニリン類の製法 |
| IL108630A0 (en) * | 1993-02-18 | 1994-05-30 | Fmc Corp | Insecticidal substituted 2,4-diaminoquinazolines |
| JP2000516941A (ja) * | 1996-08-30 | 2000-12-19 | アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー | オゾンを用いた臭素化芳香族化合物の製造 |
| ES2381758T3 (es) * | 1998-05-11 | 2012-05-31 | Basf Se | Método para la preparación de isoxazolin-3-il-acilbencenos |
-
2001
- 2001-06-29 CZ CZ20024177A patent/CZ301413B6/cs not_active IP Right Cessation
- 2001-06-29 CA CA002413723A patent/CA2413723C/en not_active Expired - Fee Related
- 2001-06-29 EP EP01947430A patent/EP1296965B1/de not_active Expired - Lifetime
- 2001-06-29 SK SK1797-2002A patent/SK285627B6/sk not_active IP Right Cessation
- 2001-06-29 DE DE50107619T patent/DE50107619D1/de not_active Expired - Lifetime
- 2001-06-29 KR KR1020027017711A patent/KR100779315B1/ko not_active Expired - Fee Related
- 2001-06-29 DK DK01947430T patent/DK1296965T3/da active
- 2001-06-29 BR BRPI0112121-9A patent/BRPI0112121B1/pt not_active IP Right Cessation
- 2001-06-29 ES ES01947430T patent/ES2250425T3/es not_active Expired - Lifetime
- 2001-06-29 NZ NZ523825A patent/NZ523825A/en unknown
- 2001-06-29 HU HU0301741A patent/HUP0301741A3/hu unknown
- 2001-06-29 AU AU6911101A patent/AU6911101A/xx active Pending
- 2001-06-29 AU AU2001269111A patent/AU2001269111B2/en not_active Ceased
- 2001-06-29 AT AT01947430T patent/ATE305928T1/de active
- 2001-06-29 JP JP2002507793A patent/JP4937485B2/ja not_active Expired - Lifetime
- 2001-06-29 PL PL359155A patent/PL206026B1/pl not_active IP Right Cessation
- 2001-06-29 CN CNB018119417A patent/CN1182124C/zh not_active Expired - Lifetime
- 2001-06-29 EA EA200300012A patent/EA006293B1/ru not_active IP Right Cessation
- 2001-06-29 WO PCT/EP2001/007482 patent/WO2002002537A1/de not_active Ceased
- 2001-06-29 IL IL15341201A patent/IL153412A0/xx active IP Right Grant
- 2001-06-29 MX MXPA02012483A patent/MXPA02012483A/es active IP Right Grant
-
2002
- 2002-12-12 IL IL153412A patent/IL153412A/en unknown
- 2002-12-23 NO NO20026201A patent/NO324408B1/no not_active IP Right Cessation
-
2003
- 2003-01-29 ZA ZA200300816A patent/ZA200300816B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RECP | Rectifications of patent specification | ||
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20110629 |