2-Aminobenzimidazole → N1-(1H-benzo[d]imidazol-2-yl)propane-1,3-diamine

HRID 1179335Notes

Reaction equation

HRID 1179335 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[NH:4][C:5]([NH:7][CH2:8][CH2:9][CH2:10][NH:11]C(=O)[O-])=S.NC1NC2C=CC=CC=2N=1>>[NH:4]1[C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[N:1]=[C:5]1[NH:7][CH2:8][CH2:9][CH2:10][NH2:11]

Participants

3

Reactant 2

HCID 136242-AminobenzimidazoleHCID 86591654HCID 86591654, compound

Product 1

HCID 11593576N1-(1H-benzo[d]imidazol-2-yl)propane-1,3-diamine

Procedure

3-{[(2-aminoanilino)carbothioyl]amino}propylcarbamate (ESI-MS; [M+H+]: 325.15), which was then converted with HgO/cat. S into the corresponding aminobenzimidazole (6.4 g; ESI-MS; [M+H+]: 291.15). After removal of the Boc group using TFA, the crude product obtained was boiled in CH3OH with addition of active carbon, filtered, evaporated and crystallized from CH3OH/methyl t-butyl ether; 6 g of beige solid; ESI-MS; [M+H+]: 191.1.

Workup

  1. customAfter removal of the Boc group

Sources & evidence

ORD record
ord-cd404ac8509147f1a400930802b4ae79
Source dataset
uspto-grants-2007_10
Patent number
US07279468B2

Reaction notes

Loading…