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

HRID 1088291노트

반응식

HRID 1088291 반응식
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

참가 물질

4

반응물 2

HCID 98641092-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazideHCID 10942334Sodium Methoxide2회

생성물 1

HCID 178425397HCID 178425397, 화합물수율 43.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8ec72fd6aab54148aab4f2cd1209ec72
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04962119

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