JPH0212476B2 - - Google Patents

Info

Publication number

JPH0212476B2

JPH0212476B2 JP23368382A JP23368382A JPH0212476B2 JP H0212476 B2 JPH0212476 B2 JP H0212476B2 JP 23368382 A JP23368382 A JP 23368382A JP 23368382 A JP23368382 A JP 23368382A JP H0212476 B2 JPH0212476 B2 JP H0212476B2

Authority

JP

Japan

Prior art keywords

formula

compound

methyl

reaction

sulfuric acid

Prior art date

1982-12-27

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Links

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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
• 150000001875 compounds Chemical class 0.000 claims description 20
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 150000008065 acid anhydrides Chemical class 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• 238000006243 chemical reaction Methods 0.000 description 14
• 238000000034 method Methods 0.000 description 8
• 239000000203 mixture Substances 0.000 description 6
• 239000013078 crystal Substances 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 238000002844 melting Methods 0.000 description 5
• 230000008018 melting Effects 0.000 description 5
• -1 2,3-dihydro-4H-1,4-benzoxazin-4-yl Chemical group 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• BVHSAZFNVBBGNX-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC(F)=C(F)C2=C1NC(C)CO2 BVHSAZFNVBBGNX-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 238000000921 elemental analysis Methods 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
• GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
• XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 description 1
• NVKWWNNJFKZNJO-UHFFFAOYSA-N 82419-35-0 Chemical compound O1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(F)C(F)=C3 NVKWWNNJFKZNJO-UHFFFAOYSA-N 0.000 description 1
• SNTZGENQEQKPHV-UHFFFAOYSA-N O1CC=NC2=CC(C(=O)OCC)=CC=C21 Chemical compound O1CC=NC2=CC(C(=O)OCC)=CC=C21 SNTZGENQEQKPHV-UHFFFAOYSA-N 0.000 description 1
• TZSXJUSNOOBBOP-UHFFFAOYSA-N ac1mwmhd Chemical compound CC1COC2=C(F)C(F)=CC3=C2N1C=C(C(=O)OCC)C3=O TZSXJUSNOOBBOP-UHFFFAOYSA-N 0.000 description 1
• YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
• 238000009776 industrial production Methods 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 229920000137 polyphosphoric acid Polymers 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000002699 waste material Substances 0.000 description 1