2-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide → HCID 178425397、化合物

HRID 973956ノート

反応式

HRID 973956 の反応式
C[O-].[Na+].[NH2:4][C:5](=[S:26])[NH:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH3:23])[C:17]=1[Cl:24]>CO>[Cl:24][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]1[NH:4][C:5](=[S:26])[NH:6][N:7]=1

参加物

4

反応物 2

HCID 98641092-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazideHCID 10942334Sodium Methoxide2 回

生成物 1

HCID 178425397HCID 178425397、化合物収率 43.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium methoxide (734.0 mg, 13.59 mmol) is added to a solution of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)-hydrazide (1.466 g, 3.96 mmol) in 60 ml of methanol and the mixture is heated at reflux overnight, under a nitrogen atmosphere. An additional amount of sodium methoxide (702.0 mg, 13.00 mmol) is added and heating at reflux is continued overnight. The volatiles are removed in vacuo and the residue dissolved in water. The aqueous solution is acidified to pH 4-5 with 10% hydrochloric acid. The resultant white solid is collected, dissolved in tetrahydrofuran and chromatographed, eluting with hexane:ethyl acetate (1:2) to give 599.2 mg (43%) of 5-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, mp 300°-305° C.

後処理

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight, under a nitrogen atmosphere
  3. temperatureheating
  4. temperatureat reflux
  5. customThe volatiles are removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. customThe resultant white solid is collected
  8. dissolutiondissolved in tetrahydrofuran
  9. customchromatographed
  10. washeluting with hexane:ethyl acetate (1:2)

出典と根拠

ORDレコード
ord-5bc840694d93412287f526dfa2fef373
出典データセット
uspto-grants-1991_11
特許番号
US05066668

反応ノート

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