Phenyl isocyanate → N-[2,6-bis(1-Methylethyl)phenyl]-2-[(diphenylmethyl)[(phenylamino)carbonyl]amino]acetamide

HRID 465654Notes

Reaction equation

HRID 465654 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:14]=1[NH:22][C:23](=[O:39])[CH2:24][NH:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:12]>CCOC(C)=O>[CH3:12][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:20])[CH3:21])[C:14]=1[NH:22][C:23](=[O:39])[CH2:24][N:25]([CH:26]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9])[CH3:10]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 1645639N-[2,6-bis(1-Methylethyl)phenyl]-2-[(diphenylmethyl)amino]acetamide

Product 1

HCID 19874922N-[2,6-bis(1-Methylethyl)phenyl]-2-[(diphenylmethyl)[(phenylamino)carbonyl]amino]acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Excess phenylisocyanate (0.44 g) was added to a mixture of the product from Example 4 (0.60 g) in 100 mL EtOAc at room temperature. After sitting for a short period of time at room temperature, the solvent was removed in vacuo. EtOAc was added to the residue and allowed to sit 2 days at room temperature. The ethyl acetate was removed on the rotary evaporator. The residual solid was slurried in hexane/EtOAc, 1/1 and collected by filtration. (0.82 g) (100%). NMR (CDCl3) δ 1.06 (12H, d), δ 2.66 (2H, m), δ 4.24 (2H, s), δ 6.44 (1H, bs), δ 6.9-7.5 (18H, m), δ 7.93 (1H, bs). IR (KBr) 3391, 2964, 1648, 1531, 1444, 752, 700 cm-1.

Workup

  1. waitAfter sitting for a short period of time at room temperature
  2. customthe solvent was removed in vacuo
  3. additionEtOAc was added to the residue
  4. customThe ethyl acetate was removed on the rotary evaporator
  5. filtration1/1 and collected by filtration

Sources & evidence

ORD record
ord-044a2cc4afe5461db9f31ac338a6ec33
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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