Phenyl isocyanate → HCID 22405575, compound

HRID 441199Notes

Reaction equation

HRID 441199 reaction equation
[NH2:1][C:2]1[C:3](=[O:22])[N:4]([CH2:8][C:9]([NH:11][CH:12]([CH:19]([CH3:21])[CH3:20])[CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>ClCCl>[O:22]=[C:3]1[C:2]([NH:1][C:30]([NH:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:31])=[CH:7][CH:6]=[CH:5][N:4]1[CH2:8][C:9]([NH:11][CH:12]([CH:19]([CH3:20])[CH3:21])[C:13](=[O:18])[C:14]([F:15])([F:16])[F:17])=[O:10]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8857Ethyl AcetateHCID 10064663HCID 10064663, compound

Product 1

HCID 22405575HCID 22405575, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Amino-2-oxo-1,2-dihydro-1-pyridyl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.43 g) and phenylisocyanate (0.175 g) were combined in dichloromethane (5 mL) and allowed to stir overnight. The mixture was poured into ethyl acetate, washed (saturated aqueous sodium bicarbonate, brine), evaporated, and purified using chromatography, eluting with ethyl acetate:dichloromethane (gradient, 0:100, 50:50, 100:0), to give the urea (0.54 g).

Workup

  1. washwashed (saturated aqueous sodium bicarbonate, brine)
  2. customevaporated
  3. custompurified
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-dd86827e03c942af99139d05611368b8
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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