Diethyl Ether → N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea

HRID 2295042Notes

Reaction equation

HRID 2295042 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:18]=[C:19]=[S:20])=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][NH2:23].CCOCC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:23][CH2:22][CH2:21][NH2:24])=[S:20])=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3301EthylenediamineHCID 214727251h-Benzimidazole-1-carboxylic acid,5-isothiocyanato-4-methyl-,1,1-dimethylethyl ester

Product 1

HCID 21472715N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-tert-butoxycarbonyl-4-methyl-5-benzimidazolylisothiocyanate (7.0 g) in CH2Cl2 (600 mL) is added dropwise over 45 minutes to ethylenediamine (8 mL) in solution in CH2Cl2 (200 mL). The mixture is stirred for 3 hours at room temperature. Ether (150 mL) is added to the suspension and the mixture is stirred for 10 minutes at room temperature. The solid is filtered. The filtrate is rotary evaporated, the residue diluted with CH2Cl2 and reprecipitated with ether to afford a second crop. The combined solids are dried overnight in vacuo to afford N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea as a white solid.

Workup

  1. stirringthe mixture is stirred for 10 minutes at room temperature
  2. filtrationThe solid is filtered
  3. additionthe residue diluted with CH2Cl2
  4. customreprecipitated with ether
  5. customto afford a second crop
  6. customThe combined solids are dried overnight in vacuo

Sources & evidence

ORD record
ord-8f169e0c948b4018ad2b8fcac3252a23
Source dataset
uspto-grants-1997_11
Patent number
US05691370

Reaction notes

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