Ethyl Acetate → 1-(2-Chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea

HRID 2278947Notes

Reaction equation

HRID 2278947 reaction equation
Cl.[F:2][C:3]([F:9])([F:8])[O:4][CH2:5][CH2:6][NH2:7].[H-].[Na+].[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].CCOC(C)=O>C1COCC1>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([NH:7][CH2:6][CH2:5][O:4][C:3]([F:9])([F:8])[F:2])=[O:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 448908072-(Trifluoromethoxy)ethan-1-amine hydrochloride

Product 1

HCID 904257591-(2-Chloroethyl)-3-(2-(trifluoromethoxy)ethyl)ureaYield 140%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. suspension of 2-(trifluoromethoxy)ethylamine hydrochloride (0.308 g, 1.861 mmol) in THF (10 mL) was treated with NaH (60% in mineral oil, 0.082 g, 2.047 mmol), stirred at 0° C. for 0.5 h, treated drop-wise with 2-chloroethyl isocyanate (0.175 mL, 2.047 mmol), allowed to warm to RT and stirred overnight. The mixture was treated with EtOAc, the solids removed via filtration and the filtrate concentrated to dryness to afford 1-(2-chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea (610 mg, 140%) containing EtOAc. 1H NMR (400 MHz, DMSO-d6): δ 6.29 (br s, 2 H), 4.04-3.97 (m, 2 H), 3.55 (t, J=6.2 Hz, 2 H), 3.33-3.24 (m, 4 H).

Workup

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. customthe solids removed via filtration
  4. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-6c489c2a969341599c02bd99165fbf6a
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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