Phenyl isocyanate → US10752598, Example 20

HRID 264031Notes

Reaction equation

HRID 264031 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:20].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[O:9]=[C:8]1[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3](=[O:20])[CH:2]1[NH:1][C:28]([NH:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:29]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 106832523-Amino-1-phenyl-1,5-dihydrobenzo[b][1,4] diazepine-2,4-dione

Product 1

HCID 10667855US10752598, Example 20Yield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 3-amino-1-phenyl-1,5-dihydro-benzo [b] [1,4]-diazepine-2,4-dione (0.398 g) in dichloromethane (5 ml) was added phenyl isocyanate (0.177 g) gradually with stirring at ambient temperature. The reaction mixture was stirred two hours at ambient temperature after which time a cream precipitate Was separated by filtration to provide the title compound (0.413 g). 1H NMR (300 MHz, DMSO-d6): d 4.97 (d, J=7.5 Hz, 1H), 6.88-6.97 (m, 3H), 7.13-7.47 (m, 12H), 9.16 (s, 1H), 10.78 (br s, 1H); TLC (CH2Cl2 /CH3OH, 19:1 ): Rf =0.21.

Workup

  1. stirringThe reaction mixture was stirred two hours at ambient temperature after which time a cream precipitate
  2. customWas separated by filtration

Sources & evidence

ORD record
ord-ee8d95080d8f47f6a706a20c076f6115
Source dataset
uspto-grants-1997_07
Patent number
US05646140

Reaction notes

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