Chlorosuccinimide → 2-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)-methylthiopropanal-1-oxime

HRID 973683노트

반응식

HRID 973683 반응식
ClN1C(=O)CCC1=O.O=[C:10]([CH3:14])[CH:11]=[N:12][OH:13].[CH3:15][S-:16].[Na+].[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([Cl:29])[C:20]=1[NH:30][NH2:31]>CN(C)C=O.O>[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([F:26])([F:28])[F:27])[CH:22]=[C:21]([Cl:29])[C:20]=1[NH:30][N:31]=[C:10]([CH2:14][S:16][CH3:15])[CH:11]=[N:12][OH:13]

참가 물질

7

반응물 4

HCID 31398ChlorosuccinimideHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 4378561Sodium methanethiolateHCID 63992132-Oxopropanal-1-oxime

생성물 1

HCID 1372254742-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)-methylthiopropanal-1-oxime

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매2회

실험 절차

N-Chlorosuccinimide (7.3 g) was added, portionwise, to a solution of 2-oxopropanal 1-oxime (4.8 g) in dimethylformamide (30 ml). The reaction was heated to 50° and hydrochloric acid gas bubbled through to initiate the reaction. The mixture was then stirred at room temperature for an hour. Poured into water, extracted with ether and the extracts worked up to give crude 1-chloro--oxopropanal 1-oxime. This (1.5 g) in dimethylformamide (25 ml) was then reacted with sodium methanethiolate (0.86 g). After 5 hours at below 5°, the mixture was poured into water and extracted with ether and the extracts worked up to give crude 1-methylthio-oxopropanal 1-oxime. This (1.0 g) was then reacted with 2,6-dichloro-4-trifluoromethylphenylhydrazine (1.84 g), in a similar to that described in Example 1, to give 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)-methylthiopropanal-1-oxime. This (1.4 g) was then reacted with acetic anhydride, in a similar manner to Example 5, to give 2-(2,6-dichloro-4-trifluoromethyl-phenylhydrazono)-1-methylthiopropanal 1-acetyloxime. This (1.4 g) was then stirred with a mixture of caesium carbonate (1.1 g) and tetrahydrofuran (40 ml) at room temperature for 2 hours. Solvent was removed and the residue worked up to give compound 3.

후처리

  1. temperatureThe reaction was heated to 50°
  2. customhydrochloric acid gas bubbled through
  3. customthe reaction
  4. extractionextracted with ether
  5. customto give crude 1-chloro--oxopropanal 1-oxime
  6. extractionextracted with ether
  7. customto give crude 1-methylthio-oxopropanal 1-oxime

출처 및 근거

ORD 기록
ord-2fb27871f2bc486d8c73989dad4e244d
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064844

반응 노트

불러오는 중…