Ethanamine, 2,2,2-trifluoro- → 1-(3-Bromophenyl)-3-(2,2,2-trifluoroethyl)urea

HRID 2400320

Reaction equation

HRID 2400320 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[F:11][C:12]([F:16])([F:15])[CH2:13][NH2:14]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:14][CH2:13][C:12]([F:16])([F:15])[F:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 1410013-Bromophenyl isocyanate

Product 1

HCID 472525331-(3-Bromophenyl)-3-(2,2,2-trifluoroethyl)ureaYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromophenyl isocyanate (1.0 ml, 8.1 mmol) was added slowly to a stirred solution of 2,2,2-trifluoroethyl amine (3.2 ml, 40 mmol) in THF (10 ml) at 0° C. under N2. After 1 hour the reaction was allowed to warm to RT and kept at this temperature for 16 hours. The volatiles were removed in vacuo to give the title compound (2.5 g, solid). 1H NMR (400 MHz, DMSO-d6): 9.00 (1H, s), 7.86 (1H, t), 7.33 (1H, ddd), 7.26 (1H, t), 7.18 (1H, ddd), 6.89 (1H, t), 4.03-3.92 (2H, m).

Workup

  1. waitkept at this temperature for 16 hours
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-237e8facd7a344d0bc52481de0880da3
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Linked notes

Loading…