Triethylamine → (R)-1-Benzoyl-3-(1-methyl-2,2,2-trifluoroethyl)-thiourea

HRID 1191078노트

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HRID 1191078 반응식
Cl.[CH3:2][C@@H:3]([NH2:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)(Cl)Cl>[C:16]([NH:24][C:25]([NH:8][C@H:3]([CH3:2])[C:4]([F:7])([F:6])[F:5])=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 68284Benzoyl isothiocyanateHCID 44593757(R)-2-Amino-1,1,1-trifluoropropane hydrochloride

생성물 1

HCID 58495475(R)-1-Benzoyl-3-(1-methyl-2,2,2-trifluoroethyl)-thiourea수율 90%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
0 °C

실험 절차

Dissolve (R)-1-methyl-2,2,2-trifluoroethylamine hydrochloride (3.73 g, 25 mmol) in chloroform (50 mL) containing triethylamine (3.5 mL, 25 mmol). Cool to 0° C. in an ice bath and dropwise add benzoyl isothiocyanate (3.35 mL, 25 mmol) over 10 min. Warm the mixture to room temperature and stir overnight. Concentrate in vacuo and purify by chromatography on silica gel (200 g) eluting with hexane/EtOAc (19:1 to 4:1 over 40 min; 50 mL/min) to afford the desired intermediate as a light yellow oil (6.2 g, 90%).

후처리

  1. temperatureWarm the mixture to room temperature
  2. concentrationConcentrate in vacuo
  3. custompurify by chromatography on silica gel (200 g)
  4. washeluting with hexane/EtOAc (19:1 to 4:1 over 40 min; 50 mL/min)

출처 및 근거

ORD 기록
ord-01c43b2f15e1481982cab6dbf9c8623c
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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