Potassium cyanate → (S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)urea

HRID 588114Notes

Reaction equation

HRID 588114 reaction equation
[NH2:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([CH3:6])([OH:5])[CH3:4].[O-:13][C:14]#[N:15].[K+]>O>[OH:5][C:3]([CH3:6])([CH3:4])[C@@H:2]([NH:1][C:14]([NH2:15])=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 46941324(S)-1-amino-2-methyl-1-phenylpropan-2-ol

Product 1

HCID 92170521(S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (S)-1-amino-2-methyl-1-phenylpropan-2-ol (2.0 g, 10 mmol) in H2O (10 mL) was added potassium cyanate (0.85 g, 12 mmol) and the contents were stirred at ambient temperature for 2 h. The solid thus obtained was filtered and washed successively with H2O (2×5 mL) and dried in air to afford (S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)urea. 1H NMR (400 MHz, DMSO-d6) δ 7.25-7.15 (m, 5H), 6.52 (d, J=9.2 Hz, 1H), 5.50 (s, 2H), 4.50 (s, 1H), 4.41 (d, J=9.2 Hz, 1H), 1.10 (s, 3H), 0.93 (s, 3H). Anal. Calcd. C11H16N2O2 208.3. Found 209.2 (M+H).

Workup

  1. customThe solid thus obtained
  2. filtrationwas filtered
  3. washwashed successively with H2O (2×5 mL)
  4. customdried in air

Sources & evidence

ORD record
ord-d682412ad1d74b478c948f816e3d76a5
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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