Hydrochloric Acid → 1-Amino-1-isopropyl-3-(2,2,2-trifluoroethyl)urea hydrochloride

HRID 1502786Notes

Reaction equation

HRID 1502786 reaction equation
[ClH:1].[CH:2]([N:5]([C:14](=[O:21])[NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])[NH:6]C(=O)OC(C)(C)C)([CH3:4])[CH3:3]>O1CCOCC1>[ClH:1].[CH:2]([N:5]([C:14]([NH:15][CH2:16][C:17]([F:18])([F:19])[F:20])=[O:21])[NH2:6])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86722583tert-butyl N-[isopropyl(2,2,2-trifluoroethylcarbamoyl)amino]carbamate

Product 1

HCID 867225801-Amino-1-isopropyl-3-(2,2,2-trifluoroethyl)urea hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4 M in dioxane, 10 mL) was added to a stirred solution of tert-butyl N-[isopropyl(2,2,2-trifluoroethylcarbamoyl)amino]carbamate (530 mg, 1.77 mmol) in 1,4-dioxane (5 mL) at 0° C. and the reaction mixture was stirred at ambient temperature for 2 h. The volatiles were evaporated and the residue was washed with pentane to afford the title compound as a pale yellow solid. (360 mg, crude): 1H NMR (300 MHz, DMSO-d6) δ 11.2 (bs, 2H), 9.81 (s, 1H), 6.98 (t, J=6.3 Hz, 1H), 3.90-3.80 (m, 2H), 3.07-3.03 (m, 1H), 1.18 (d, J=6.6 Hz, 6H); 13C NMR (300 MHz, DMSO-d6) δ 157.06, 126.90, 52.25, 45.33, 17.49; 19F NMR (300 MHz, DMSO-d6) δ −71.52; ESIMS m/z 200.0 ([M−HCl]+).

Workup

  1. customThe volatiles were evaporated
  2. washthe residue was washed with pentane

Sources & evidence

ORD record
ord-57b299a75f9d41c1b340add427295937
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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