Phenyl isocyanate → HCID 131718858, compound

HRID 274812Notes

Reaction equation

HRID 274812 reaction equation
[NH2:1][CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]([NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11]([NH:10][CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:1][C:36]([NH:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:37])=[O:12])=[CH:15][CH:16]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 18691618HCID 18691618, compound

Product 1

HCID 131718858HCID 131718858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [R-(R*,R*)] and [S-(R*,R*)]N-(2-amino-1,2 -diphenylethyl)-N'-(4-nitrophenyl)urea (0.1 g, 0.27 mmol) in dichloromethane (10 mL) is added phenyl isocyanate (0.03 g, 0.27 mmol) in one portion. The resulting mixture is stirred 1 hour at room temperature before filtering off the solid product. The product is suspended in hot diethyl ether, filtered, and dried in vacuo at 114° C. for 4 hours, mp 246°-247° C. IR (KBr): 3355, 1656, 1554, 1498, 1330, 1233, 699 cm-1 ; NMR (DMSO-d6): 5.03 (m, 2H), 6.55-7.37 (m, 17H), 7.59 (d, 2H, J=9.2 Hz), 8.11 (d, 2H, J=9.2 Hz), 8.60 (s, 1H), 9.43 (s, 1H). Analysis calculated for C28H25 5O4.1.0H2O: C, 65.49; H, 5.30; N, 13.64. Found: C, 65.44; H, 5.03; N, 13.77.

Workup

  1. filtrationbefore filtering off the solid product
  2. filtrationfiltered
  3. customdried in vacuo at 114° C. for 4 hours

Sources & evidence

ORD record
ord-109bb513a1f74397885456bc11e4b4f5
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

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