SU181654A1 - - Google Patents
Info
- Publication number
- SU181654A1 SU181654A1 SU1005663A SU1005663A SU181654A1 SU 181654 A1 SU181654 A1 SU 181654A1 SU 1005663 A SU1005663 A SU 1005663A SU 1005663 A SU1005663 A SU 1005663A SU 181654 A1 SU181654 A1 SU 181654A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aromatic aldehydes
- chloride
- methylbenzimidazole
- dimethylformamide
- yield
- Prior art date
Links
- 150000003934 aromatic aldehydes Chemical class 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- TYMOZADWWQAIQB-UHFFFAOYSA-N 2-methylbenzimidazole Chemical compound C1=C[CH]C2=NC(C)=NC2=C1 TYMOZADWWQAIQB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- QQLPPRIZUPEKMV-UHFFFAOYSA-N 2-(2-phenylethenyl)-1H-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C=CC1=CC=CC=C1 QQLPPRIZUPEKMV-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Description
СПОСОБ ПОЛУЧЕНИЯ 2-СТИРИЛБЕНЗИМИДАЗОЛОВMethod for producing 2-styrylbenzimidazole
Известен снособ получени 2-стирилбенз11мидазолоБ взаимодействиел 2-метнлбензимндазола с ароматическими альдегидами в присутствии безводного хлористого цинка.A method for preparing 2-styrylbenz1midazoloB is known to react 2-methylbenzimndazole with aromatic aldehydes in the presence of anhydrous zinc chloride.
Предлагаемый способ получени 2-стирилбеизимидазолов заключаетс во взаимодействии 2-метилбензимидазола с ароматическими альдегидами в среде диметилформамида в присутствии хлористого бензоила. Образующиес промежуточные -ацильные соли 2-метилбеизнмидазола легко реагируют с ароматическими альдегидами, что упрощает процесс , а также повыщает выход целевых продуктов .The proposed method for the preparation of 2-styrylbemiimidazoles consists in the interaction of 2-methylbenzimidazole with aromatic aldehydes in dimethylformamide in the presence of benzoyl chloride. The resulting intermediate α-acyl salts of 2-methyl-boin-imidazole react easily with aromatic aldehydes, which simplifies the process and also increases the yield of the target products.
Пример. Получение 2-га-диметиламиностирилбензимидазола .Example. Preparation of 2-g-dimethylaminosthenylbenzimidazole
К раствору 1,32 г 2-метилбензимидазола в 3 мл диметилформамида прибавл ют раствор 1,49 г п-диметиламниобеизальдегида в 2 мл диметилформамнда и при охлаждении лед ной баней и перемещиваиии прикапываютTo a solution of 1.32 g of 2-methylbenzimidazole in 3 ml of dimethylformamide was added a solution of 1.49 g of p-dimethylamineioaldehyde in 2 ml of dimethylformand and, while cooling with an ice bath and moving, drop by drop
1,426 г хлористого беизоила. Реакционную смесь, разогревщуюс до 70-SO C, выдерживают 5 час при 150-160°С, после чего разлагают сол ной кислотой и отгон ют паром, остаток отфильтровывают, сушат и перекристаллизовывают из толуола. Выход 2-/г-диметиламииостирилбензимидазола 1,74 г (66%). т. пл. 250°С. По литературным данным т. пл. 250, 259-260°С.1,426 g of beosoyl chloride. The reaction mixture, heated to 70-SO C, is kept at 150-160 ° C for 5 hours, after which it is decomposed with hydrochloric acid and distilled with steam, the residue is filtered, dried and recrystallized from toluene. The output of 2- / g-dimethylamine austilbenzimidazole 1.74 g (66%). m.p. 250 ° C. According to literary data, m. Pl. 250, 259-260 ° C.
Аналогично протекает конденсаци и с другими ароматическими альдегидами.Similarly, condensation proceeds with other aromatic aldehydes.
Предмет изобретени Subject invention
Способ получени 2-стирилбензимидазолоп иа основе 2-метилбензимидазола и ароматических альдегидов, отличающийс тем, что, с целью сокращени времени проведени процесса и повьинени выхода, процесс ведут вThe method of producing 2-styrylbenzimidazolop based on 2-methylbenzimidazole and aromatic aldehydes, characterized in that, in order to shorten the process time and yield, the process is carried out
присутствии хлористого беизопла в среде диметн л форм амида.in the presence of chloride of beisopl in the medium dimethyl forms of amide.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU181654A1 true SU181654A1 (en) |
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