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

HRID 1093527

Reaction equation

HRID 1093527 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-e70da5e8874749b9bfe1db8b1b02fe8f
Source dataset
uspto-grants-2012_03
Patent number
US08131527B1

Linked notes

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