Formic Acid → 5'-fluoro-N-methyl-2'-(methylthio)acetylformanilide

HRID 1089768ノート

反応式

HRID 1089768 の反応式
[C:1](OC(=O)C)(=O)C.C(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:22])[CH2:19][S:20][CH3:21])=[C:14]([NH:23][CH3:24])[CH:13]=1.[OH2:25]>>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:22])[CH2:19][S:20][CH3:21])=[C:14]([CH:13]=1)[N:23]([CH3:1])[CH:24]=[O:25]

参加物

5

反応物 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 199784741-(4-Fluoro-2-methylaminophenyl)-2-(methylthio)ethanone

生成物 1

HCID 867447405'-fluoro-N-methyl-2'-(methylthio)acetylformanilide

実験手順

A mixture of acetic anhydride (16.5 ml) and formic acid (11.2 ml) was stirred and heated at 50°-60° under nitrogen for 2 hours. The mixture was cooled to ambient temperature and 1-(4-fluoro-2-methylaminophenyl)-2-(methylthio)ethanone (4.0 g), prepared in a similar manner to that described in Example 4, added over a period of 5 minutes. The mixture was stirred at ambient temperature for 2.75 hours and then cooled in an ice/salt bath to maintain the temperature below 30° whilst, water (50 ml) was added over a period of 30 minutes. The mixture was extracted with dichloromethane (2×25 ml), the organic phases combined, washed with water (2×20 ml) and then evaporated in vacuo to give an oily product. Purification of the oily product by high performance liquid chromatography carried out using a Gilson system fitted with a 2" Dynamax silica column and eluting with dichloromethane/methanol (99:1) at 16 ml/min gave 5'-fluoro-N-methyl-2'-(methylthio)acetylformanilide in the form of a pale yellow oil.

後処理

  1. temperatureheated at 50°-60° under nitrogen for 2 hours
  2. additionadded over a period of 5 minutes
  3. stirringThe mixture was stirred at ambient temperature for 2.75 hours
  4. temperaturecooled in an ice/salt bath
  5. additionwas added over a period of 30 minutes
  6. extractionThe mixture was extracted with dichloromethane (2×25 ml)
  7. washwashed with water (2×20 ml)
  8. customevaporated in vacuo
  9. customto give an oily product
  10. customPurification of the oily product by high performance liquid chromatography
  11. customfitted with a 2" Dynamax silica column
  12. washeluting with dichloromethane/methanol (99:1) at 16 ml/min

出典と根拠

ORDレコード
ord-100ae3f7bb5f4cdf899760d9a6bfa8aa
出典データセット
uspto-grants-1992_01
特許番号
US05079264

反応ノート

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