Cyclohexyl isocyanate → HCID 70268737, compound

HRID 274813Notes

Reaction equation

HRID 274813 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.[CH:29]1([N:35]=[C:36]=[O:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>ClCCl>[CH:29]1([NH:35][C:36]([NH:1][CH:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:12])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 18691618HCID 18691618, compound

Product 1

HCID 70268737HCID 70268737, 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 cyclohexyl 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 244°-245° C. IR (KBr): 3337, 2931, 1639, 1559, 1507, 1330, 700 cm-1 ; NMR (DMS-d6): 0.97-1.66 (m, 10H), 4.94 (m, 2H), 5.94 (d, 1H, J=7.5 Hz), 6.42 (d, 1H, J=7.5 Hz), 7.03-7.19 (m, 12H), 7.60 (d, 2H, J=9.2 Hz), 8.12 (d, 2H, J=9.2 Hz), 9.51 (s, 1H). Analysis calculated for C 28 H31N5O4 : C, 67.05; H, 6.23; N, 13.96. Found: C, 66.74; H, 6.22; N, 13.98.

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-8072d8a4128e4a29a46bc6b852c264d7
Source dataset
uspto-grants-1995_02
Patent number
US05389682

Reaction notes

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