Methyl chloroformate → HCID 145820994, compound

HRID 1647892Notes

Reaction equation

HRID 1647892 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:22])=[CH:20][C:13]=3[N:12]=2)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].C(N(C(C)C)C(C)C)C.Cl[C:40]([O:42][CH3:43])=[O:41]>C(Cl)Cl>[CH3:43][O:42][C:40]([NH:4][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:22])=[CH:20][C:13]=3[N:12]=2)=[CH:7][CH:6]=1)=[NH:3])=[O:41]

Participants

5

Reactant 3

HCID 6586Methyl chloroformate3×HCID 81531Diisopropylethylamine3×HCID 19921272HCID 19921272, compound

Product 1

HCID 145820994HCID 145820994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.26 g of 2-(4-amidino-phenyl)-5-[(2-methoxycarbonyl-ethyl)-aminocarbonyl]-1-methyl-benzimidazole-hydrochloride are suspended in 50 ml of methylene chloride and, whilst cooling with ice, 0.5 ml of N-ethyl-diisopropylamine and 0,067 ml of methyl chloroformate are added. The mixture is stirred at ambient temperature, after half an hour a further 0.5 ml of N-ethyl-diisopropylamine and 0.03 ml of methyl chloroformate are added and, after another half hour, a further 0.1 ml of N-ethyl-diisopropylamine and 0.03 ml of methyl chloroformate. The mixture is stirred for a further half hour, evaporated down in vacuo and purified by column chromatography (silica gel; eluant:ethyl acetate/ethanol=100:2.5 to 100:12.5). Yield: 0.12 g (40% of theory), Rf value: 0.41 (silica gel; ethyl acetate/ethanol=8:2)

Workup

  1. additionare added
  2. additionare added and, after another half hour
  3. customevaporated down in vacuo
  4. custompurified by column chromatography (silica gel; eluant:ethyl acetate/ethanol=100:2.5 to 100:12.5)

Sources & evidence

ORD record
ord-680c2294dcf54a958c663bfe0445ad07
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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