Triethylamine → N-Methyl-N-(3-methyl-1,2,4-thiadiazol-5-yl)cyclohexanecarboxamide

HRID 1862807ノート

反応式

HRID 1862807 の反応式
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][NH:11][C:12]1[S:16][N:15]=[C:14]([CH3:17])[N:13]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:17][C:14]1[N:13]=[C:12]([N:11]([CH3:10])[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[S:16][N:15]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 12725101N,3-Dimethyl-1,2,4-thiadiazol-5-amine

生成物 1

HCID 20393633N-Methyl-N-(3-methyl-1,2,4-thiadiazol-5-yl)cyclohexanecarboxamide

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Cyclohexane carboxylic acid chloride (9.92 g, 0.068 mol) was added slowly to a solution of 5-methylamino-3-methyl-1,2,4-thiadiazole (7.0 g, 0.054 mol) in dry benzene containing triethylamine (6.87 g, 0.068 mol) and the mixture heated under reflux for 11/2 hours, cooled and washed with 2 N hydrochloric acid, saturated solution sodium hydrogen carbonate and water; dried over magnesium sulphate, filtered and evaporated down to yield yellow oil which crystallised upon standing. This was recrystallised twice from petroleum ether 60°-80° C. to yield off-white crystals of N-(3-methyl-1,2,4-thiadiazol-5-yl)-N-methylcyclohexane carboxamide. Yield 8.23 g, (63.8%), m.p. 96° C.

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 11/2 hours
  3. temperaturecooled
  4. washwashed with 2 N hydrochloric acid, saturated solution sodium hydrogen carbonate and water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated down
  8. customto yield yellow oil which
  9. customcrystallised
  10. customThis was recrystallised twice from petroleum ether 60°-80° C.

出典と根拠

ORDレコード
ord-eb4ddb7dc4c241cabcafa834a7eac3e1
出典データセット
uspto-grants-1979_09
特許番号
US04166818

反応ノート

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