Phenyl isocyanate → HCID 69748017, compound

HRID 2301046Notes

Reaction equation

HRID 2301046 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:26]([NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:13])([F:15])[F:14]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 54520116HCID 54520116, compound

Product 1

HCID 69748017HCID 69748017, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (R)-N-[2-chloro-4-aminophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 208) (0.198 g) and phenyl isocyanate (0.09 ml) in diethyl ether (10 ml) was stirred for 22 hours then evaporated to dryness. The residue was partitioned between water (25 ml) and ethyl acetate (50 ml). The organic phase was washed with brine (25 ml), dried and concentrated by evaporation to give the title compound (170 mg) as a foam. NMR: 1.66 (s, 3H), 7.04 (t, 1H), 7.35 (m, 3H), 7.52 (d, 1H), 7.1 (s, 1H), 7.86 (m, 2H), 8.77 (s, 1H), 8.92 (s, 1H), 9.63 (s, 1H); MS (ESP−): 400.

Workup

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between water (25 ml) and ethyl acetate (50 ml)
  3. washThe organic phase was washed with brine (25 ml)
  4. customdried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b9207fdf0d8e46bf83fd80f5f41248cf
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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