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

HRID 341248

Reaction equation

HRID 341248 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 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromophenyl isocyanate (21.12 g, 107 mmol) was added slowly to a stirred solution of 2,2,2-trifluoroethyl amine (40 ml, 0.5 mol) in THF (100 mL) at 0° C. under N2, rinsing with THF (25 mL). The reaction was allowed to warm slowly to RT and kept at this temperature for 16 hours. The volatiles were removed under reduced pressure to give the title compound (31.6 g) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (1H, s), 7.80 (1H, t), 7.31-7.24 (1H, m), 7.20 (1H, t), 7.16-7.08 (1H, m), 6.83 (1H, bt), 3.98-3.85 (2H, m).

Workup

  1. washrinsing with THF (25 mL)
  2. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-fc8ce008d32a429abfc3853292086f29
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Linked notes

Loading…