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

HRID 1191078Notes

Reaction equation

HRID 1191078 reaction equation
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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68284Benzoyl isothiocyanateHCID 44593757(2R)-1,1,1-Trifluoropropan-2-amine--hydrogen chloride (1/1)

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-01c43b2f15e1481982cab6dbf9c8623c
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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