Ethylenediamine → HCID 18400133, compound

HRID 1019088Notes

Reaction equation

HRID 1019088 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]=[C:9]1[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([NH2:25])[CH2:23][NH2:24]>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:24][CH2:23][CH2:22][NH2:25])=[S:20])=[C:16]([CH3:17])[C:11]=2[N:10]=[C:9]1[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 18400157HCID 18400157, compound

Product 1

HCID 18400133HCID 18400133, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-t-butoxycarbonyl-2,4-dimethyl-5-isothiocyanatobenzimidazole (1.15 g, 3.8 mmol) in methylene chloride (100 mL) is added dropwise over 15 minutes to 1,2-ethylenediamine (1.26 mL, 18.9 mmol) in solution in methylene chloride (200 mL). The mixture is stirred for 2 hours at room temperature. The mixture is rotary evaporated and the residue is triturated with ether (150 mL) for 1 hour at room temperature. The solid is filtered and dried in vacuo to afford N-(1-t-butoxycarbonyl-2,4-dimethyl-5-benzimidazolyl)-N′-2-aminoethylthiourea as a white solid.

Workup

  1. customThe mixture is rotary evaporated
  2. customthe residue is triturated with ether (150 mL) for 1 hour at room temperature
  3. filtrationThe solid is filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a00e79c3bf144bb0aac5752a2f8d1419
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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