Methanesulfonic Acid → 5-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-1,3,4-thiadiazol-2-amine

HRID 2211170노트

반응식

HRID 2211170 반응식
CS(O)(=O)=O.[NH2:6][C:7](=[S:28])[NH:8][NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[C:20]([CH3:25])[C:19]=1[Cl:26]>C1(C)C=CC=CC=1>[Cl:26][C:19]1[C:20]([CH3:25])=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[S:28][C:7]([NH2:6])=[N:8][N:9]=1

참가 물질

4

반응물 2

HCID 6395Methanesulfonic AcidHCID 98641092-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide

생성물 1

HCID 149513585-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]-1,3,4-thiadiazol-2-amine수율 59%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Methanesulfonic acid (280 μl, 4.31 mol) is added dropwise to a suspension of 2-[(2,6-dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide (1.008 g, 2.73 mmol) in 30 ml of toluene. The mixture is heated at reflux for three hours under a nitrogen atmosphere and allowed to cool to room temperature overnight. The tan solid is filtered off and suspended in 100 ml of ethyl acetate. The suspension is then stirred vigorously with 40 ml of 10% aqueous ammonium hydroxide, and the layers are separated. The ethyl acetate layer is washed with water, and dried over magnesium sulfate. Filtration and concentration in vacuo gives a white solid. Drying at 60° C. in vacuo overnight provides 560.8 mg (59%) of product, mp 219°-226° C.

후처리

  1. temperatureThe mixture is heated
  2. temperatureat reflux for three hours under a nitrogen atmosphere
  3. filtrationThe tan solid is filtered off
  4. customthe layers are separated
  5. washThe ethyl acetate layer is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and concentration in vacuo
  8. customgives a white solid
  9. customDrying at 60° C. in vacuo overnight

출처 및 근거

ORD 기록
ord-370bc1a58f0947b6a5efff668ee8450b
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05462952

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