Formic Acid → 1-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 555284Notes

Reaction equation

HRID 555284 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][C:13]#[N:14])=[C:6]([NH2:15])[CH:5]=1.[CH:17](O)=O>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][C:13]#[N:14])[CH:17]=[N:15][C:6]=2[CH:5]=1)=[O:16]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 669874673-Amino-4-(2-cyano-ethylamino)-benzoic acid methyl ester

Product 1

HCID 669871661-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl esterYield 95%

Conditions

Temperature
50 °C

Procedure

To 3-amino-4-(2-cyano-ethylamino)-benzoic acid methyl ester (4.0 g) was added formic acid (25 ml) and the mixture heated to 50° C. for 3 h. It was then concentrated and the residue recrystallised from EtOAc to afford 4.0 g (95%) of 1-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 230 (M+1); 1H NMR (300 MHz, CDCl3) δ 2.95 (t, 2H), 4.0 (s, 3H), 4.55 (t, 2H), 7.4 (d, 1H), 8.1 (m, 1H), 8.15 (s, 1H), 8.55 (s, 1H)

Workup

  1. concentrationIt was then concentrated
  2. customthe residue recrystallised from EtOAc

Sources & evidence

ORD record
ord-0eb1abaa14084ba58aae1766aa733892
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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