2-Aminobenzimidazole → HCID 178508672, compound

HRID 615439Notes

Reaction equation

HRID 615439 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Na].[C:12]([NH:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=S)#[N:13]>>[NH2:13][C:12]1[N:1]=[C:2]2[N:6]([C:15](=[N:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=1)[C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[NH:3]2

Participants

4

Reactant 3

HCID 136242-AminobenzimidazoleHCID 4711553N-cyano-N'-phenylthioureaHCID 5360545Sodium

Product 1

HCID 178508672HCID 178508672, compoundYield 27.8%

Procedure

A suspension of 2-aminobenzimidazole (10.0 g) and the sodium salt of N-cyano-N'-phenyl thiourea (7.5 g) was stirred at room temperature for 30 minutes. Mercuric chloride (10.2 g) was added and stirring continued for 16 h. The mixture was filtered and the filtrate evaporated to a gum. A solution of the gum in methanol soon yielded a solid (3.25 g). The solid was collected, suspended in tetrahydrofuran and hydrogen sulphide added until no further black precipitate formed. The mixture was filtered and the filtrate evaporated to give a yellow solid which showed several components on thin layer chromatography. The components were separated on a column of silica gel to give the sub-title compound as white crystals (1.22 g) mp, 271°-3°.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to a gum

Sources & evidence

ORD record
ord-3d926913d3374148bd8b350ef7ffe9ac
Source dataset
uspto-grants-1985_02
Patent number
US04499269

Reaction notes

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