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

HRID 2278964Notes

Reaction equation

HRID 2278964 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[Cl:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12]>C1COCC1>[Cl:7][CH2:8][CH2:9][NH:10][C:11]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[O:12]

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 160352-Chloroethyl isocyanate

Product 1

HCID 2604441-(2-chloroethyl)-3-(2,2,2-trifluoroethyl)ureaYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2,2-trifluoroethanamine (0.469 g, 4.74 mmol) and chloroethylisocyanate (0.50 g, 4.74 mmol) in THF (10 mL) was stirred at RT for 2 h, then concentrated to dryness. The residue was treated with DCM, concentrated to dryness and dried to afford 1-(2-chloroethyl)-3-(2,2,2-trifluoroethyl)urea (910 mg, 94%). 1H NMR (400 MHz, DMSO-d6): δ 6.67 (t, J=6.5 Hz, 1 H), 6.41 (m, 1 H), 3.80 (m, 2 H), 3.57 (t, J=6.2 Hz, 2 H), 3.32 (m, 2 H); MS (ESI) m/z: 205.0 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was treated with DCM
  3. concentrationconcentrated to dryness
  4. customdried

Sources & evidence

ORD record
ord-f8479425e1cb4e37967cb8ae87b4c4c9
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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