Hexane → N-(3,4-dichlorobenzyl)-N'-1H-indol-4-ylurea

HRID 887215Notes

Reaction equation

HRID 887215 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]=[C:20]=[O:21])=[CH:14][C:13]=1[Cl:22].CCCCCC>C1COCC1>[Cl:22][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:12]=1[Cl:11])[CH2:18][NH:19][C:20]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)=[O:21]

Participants

5

Reactant 3

HCID 8058HexaneHCID 5834314-AminoindoleHCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzene

Product 1

HCID 10042481N-(3,4-dichlorobenzyl)-N'-1H-indol-4-ylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Aminoindole (0.13 g, 1 mmol) in THF (3 mL) was treated with 1,2-dichloro-4-(isocyanatomethyl)benzene (0.22 g, 1.1 mmol) for 3 h at ambient temperature. Hexane was added to the reaction mixture to precipitate 0.25 g of the title compound as a tan solid. mp 201° C.; 1H NMR (300 MHz, DMSO-d6) δ 4.23 (d, 2H), 6.36 (s, 1H), 6.54 (t, 1H), 7.0 (dd, 1H), 7.25 (m, 2H), 7.30 (d, 2H), 7.45 (d, 1H), 7.6 (m, 2H), 8.31 (s, 1H), 10.87 (s, 1H) MS (DCI+) m/z 336 (M+H); Anal. Calcd. For C16H13N3Cl2O: C, 57.50; H, 3.92; N, 12.57. Found: C, 56.94; H, 3.68; N, 11.97.

Workup

  1. customto precipitate 0.25 g of the title compound as a tan solid

Sources & evidence

ORD record
ord-5c816fcfd9a74f8082930c851dd7fc44
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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