Hydrochloric Acid → HCID 118169033, compound

HRID 588123Notes

Reaction equation

HRID 588123 reaction equation
[F:1][CH:2]([F:13])[O:3][CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].Cl.[O-:15][C:16]#[N:17].[K+]>O>[F:1][CH:2]([F:13])[O:3][CH2:4][C@@H:5]([NH:6][C:16]([NH2:17])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 118168971HCID 118168971, compound

Product 1

HCID 118169033HCID 118169033, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-2-(difluoromethoxy)-1-phenylethanamine (169 mg, 0.903 mmol) in water (6 ml), was added HCl (3.6 ml, 3.61 mmol) 1N and potassium cyanate (366 mg, 4.51 mmol). The reaction was heated at 80° C. for 2 hrs, then allowed to cool to ambient temperature overnight. The precipitate formed was filtered, washed with water, and dried under high vacuum to provide (S)-1-(2-(difluoromethoxy)-1-phenylethyl)urea MS: [M+H]+ m/z 231. 1H NMR (500 MHz, DMSO-d6) δ 7.42-7.30 (m, 4H), 7.29-7.17 (m, 1H), 6.84-6.45 (m, 2H), 5.61 (s, 2H), 4.97-4.83 (m, 1H), 4.08-3.89 (m, 2H).

Workup

  1. temperatureto cool to ambient temperature overnight
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-c64049cc79024f93bd1f2df1c9059d21
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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