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

HRID 1191078ノート

反応式

HRID 1191078 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-01c43b2f15e1481982cab6dbf9c8623c
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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