Hydrochloric Acid → (S)-1-(2-methoxy-1-phenylethyl)urea

HRID 590775Notes

Reaction equation

HRID 590775 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH2:5].[O-:12][C:13]#[N:14].[K+].Cl>O>[CH3:1][O:2][CH2:3][C@@H:4]([NH:5][C:13]([NH2:14])=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 11768756(S)-2-Methoxy-1-phenylethanamine

Product 1

HCID 89524417(S)-1-(2-methoxy-1-phenylethyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

(S)-2-Methoxy-1-phenylethanamine (5.6 g, 37.0 mmol) and potassium cyanate (8.12 g, 100 mmol) were taken up in HCl (1 N, 40 mL, 40.0 mmol) and water (40 mL). The reaction mixture was heated to 100° C. for 3 h. Room temperature was attained, water was added, and the products extracted into EtOAc (×3) followed by 10% MeOH-DCM (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated in Et2O to give (S)-1-(2-methoxy-1-phenylethyl)urea. MS ESI calc'd. for C10H14N2O2 [M+1]+ 195. found 195.

Workup

  1. customRoom temperature
  2. extractionthe products extracted into EtOAc (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in Et2O

Sources & evidence

ORD record
ord-a12f10fb07d1414fb4d908563aea466d
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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