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

HRID 973683

反応式

HRID 973683 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2fb27871f2bc486d8c73989dad4e244d
出典データセット
uspto-grants-1991_11
特許番号
US05064844

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