Dimethylformamide → Ethyl 2-(bromoethoxyimino)-2-(2-tritylamino-4-thiazolyl)-acetate

HRID 1904133노트

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HRID 1904133 반응식
C(=O)([O-])[O-].[K+].[K+].Cl.[C:8]([NH:27][C:28]1[S:29][CH:30]=[C:31]([C:33](=[N:39][OH:40])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:32]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C)C=O.[Br:46][CH2:47][CH2:48]Br>C(Cl)Cl.O>[C:8]([NH:27][C:28]1[S:29][CH:30]=[C:31]([C:33](=[N:39][O:40][CH2:48][CH2:47][Br:46])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[N:32]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 78408569Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetate hydrochloride

생성물 1

HCID 53679114Ethyl 2-(bromoethoxyimino)-2-(2-tritylamino-4-thiazolyl)-acetate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

4.14 g of potassium carbonate were added over 3 minutes under argon at room temperature to a mixture of 4.94 g of syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetate hydrochloride and 10 ml of dimethylformamide, and after stirring the mixture at 20° C. for 20 minutes, 8.65 ml of 1,2-dibromoethane were added thereto. The mixture was stirred for 30 hours and was poured into 100 ml of distilled water and 20 ml of methylene chloride. The mixture was decanted and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried and vacuum filtered. The filter was rinsed and the filtrate was evaporated to dryness to obtain a raw product which was chromatographed over silica gel. Elution with benzene containing 5% of ether yielded a first fraction which was crystallized from methanol after dissolution at 50°-60° C. Vacuum filtration at 0° to 5° C. yielded 1.16 g of the syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-(2-bromoethoxyimino)-acetate in the form of a white cream product melting at 117° C. Next obtained was a homogenous fraction of 1.258 g of product.

후처리

  1. stirringThe mixture was stirred for 30 hours
  2. customThe mixture was decanted
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. customThe combined organic phases were dried
  5. filtrationvacuum filtered
  6. washThe filter was rinsed
  7. customthe filtrate was evaporated to dryness
  8. customto obtain a raw product which
  9. customwas chromatographed over silica gel
  10. washElution with benzene containing 5% of ether
  11. customyielded a first fraction which
  12. customwas crystallized from methanol
  13. dissolutionafter dissolution at 50°-60° C
  14. filtrationVacuum filtration at 0° to 5° C.

출처 및 근거

ORD 기록
ord-3cbbf6c321ad414e88e7adb6a1c4242d
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04439433

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