3-Isocyanatobenzonitrile → 1-(4-Bromophenethyl)-3-(3-cyanophenyl)-1-methylurea

HRID 735555Notes

Reaction equation

HRID 735555 reaction equation
Br[C:2]1[CH:7]=C[C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)=[O:13])=[CH:4][CH:3]=1.[Br:24]C1C=CC(CCNC)=CC=1.N(C1C=C(C=CC=1)C#N)=C=O>>[Br:24][C:3]1[CH:2]=[CH:7][C:8]([CH2:9][CH2:10][N:11]([CH3:23])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 27333153-IsocyanatobenzonitrileHCID 183675562-(4-Bromophenyl)-N-methylethan-1-amineHCID 578426211-(3-(4-Bromophenyl)propyl)-3-(3-cyanophenyl)-1-methylurea

Product 1

HCID 578428191-(4-Bromophenethyl)-3-(3-cyanophenyl)-1-methylureaYield 81%

Procedure

Using a procedure analogous to that used to prepare 22C, 23B (300 mg, 1.4 mmol) was reacted with 3-isocyanatobenzonitrile to yield 23C (406 g, 81%) as a clear oil. MS (ESI) m/z 358.31/360.29 (M+H)+.

Sources & evidence

ORD record
ord-3bcc7b5769f44f1cb361ed3c3eb6e860
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…