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

HRID 341227Notes

Reaction equation

HRID 341227 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-e422073e45b040e7934594738ed5d643
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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