2,3-Diaminobenzoic acid methyl ester → Methyl 2-butyl-1H-benzimidazole-4-carboxylate

HRID 129853Notes

Reaction equation

HRID 129853 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl.[C:14](=N)(OCC)[CH2:15][CH2:16][CH2:17][CH3:18]>>[CH2:15]([C:14]1[NH:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[N:1]=1)[CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 5718252,3-Diaminobenzoic acid methyl esterHCID 12283341Ethyl pentanimidate hydrochloride

Product 1

HCID 14987323Methyl 2-butyl-1H-benzimidazole-4-carboxylateYield 87.3%

Procedure

Using the procedure of Step A of Example 1, 2.5 g of methyl 2,3-diaminobenzoate [J. Chem. Soc., Vol. 117 (1920) p 775 and CAN. J. Chem., Vol.55 (1977), p. 1653 to 1657] and 2.73 g of ethyl pentanimidoate hydrochloride [J.A.C.S., Vol. 64, p. 1827 (1942)] were reacted to obtain 3.05 g of the desired product which after crystallization from essence G melted at approximately 85° C. The analytical sample was obtained by two successive crystallizations of 280 mg of product from isopropyl ether to obtain 100 mg of the product melting at 97° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3bbf215d724048a2a01b2154f80fc006
Source dataset
uspto-grants-1995_11
Patent number
US05470867

Reaction notes

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