Water → HCID 178419600, compound

HRID 415103Notes

Reaction equation

HRID 415103 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1.O.[N:14]#[C:15][Br:16]>C(#N)C>[BrH:16].[NH2:14][C:15]1[NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[CH:5][C:6]=2[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 178419600HCID 178419600, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-Diaminobenzoic acid methyl ester (58.72 mmoles, 9.35 g, 1 equivalent, commercially available from Oakwood Products) was dissolved in acetonitrile (20 ml) and water (200 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (8.64 g, 81.55 mmoles, 1.4 equivalent) was added over a period of 5 minutes, and the reaction mixture was allowed to go to room temperature and stirred for 16 hours. The reaction mixture was then evaporated under reduced pressure to 15.60 g of methyl 2-amino-1H-benzo[d]imidazole-5-carboxylate hydrobromide (yield: 98%) which was used directly in the next reaction without any further reaction. 1H-NMR (400 MHz DMSO-d6) δ 12.64 (br s, 2H), 8.80 (bs, 3H), 7.91 (s, 1H), 7.82 (d, 1H), 7.51 (d, 1H), 3.82 (s, 3H). MS (EI): 192 (MH+).

Workup

  1. customto go to room temperature

Sources & evidence

ORD record
ord-e4a82e17dd684c0db817c86fdacc4f53
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

Loading…