O-Phenylenediamine → 2,2'-(Thiobis(methylene))bis-1H-benzimidazole

HRID 1765970Notes

Reaction equation

HRID 1765970 reaction equation
[S:1]([CH2:6][C:7](O)=O)[CH2:2][C:3](O)=O.[C:10]1([NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].[NH4+:18].[OH-]>Cl>[NH:16]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:17]=[C:3]1[CH2:2][S:1][CH2:6][C:7]1[NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:18]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 14923Ammonium HydroxideHCID 31277Thiodiglycolic acid

Product 1

HCID 1183782,2'-(Thiobis(methylene))bis-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4.1 g (27.3 mmol) thiodiacetic acid and 4.9 g (27.3 mmol) o-phenylene diamine in 40 ml 4N HCl was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature an neutralised with conc. NH4OH. The formed precipitate was filtered, washed with water (3×40 ml) and dried under vacuum. Yield—2.4g (25.2%).

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationThe formed precipitate was filtered
  3. washwashed with water (3×40 ml)
  4. customdried under vacuum
  5. customYield—2.4g (25.2%)

Sources & evidence

ORD record
ord-e8e4945a4b8e473bb2a6c2b863f34abe
Source dataset
uspto-grants-2007_06
Patent number
US07229943B2

Reaction notes

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