Ethanol → HCID 178527766, compound

HRID 1723153Notes

Reaction equation

HRID 1723153 reaction equation
[N:1]1([CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:21](=S)=[S:22].C(O)C.[OH-].[K+]>O>[N:1]1([CH:6]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:7]2[CH:12]=[CH:11][C:10]3[NH:13][C:21]([SH:22])=[N:14][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 14990928HCID 14990928, compound

Product 1

HCID 178527766HCID 178527766, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.28 parts of 4-[(1H-imidazol-1-yl)phenylmethyl]-1,2-benzenediamine, 2.3 parts of carbon disulfide, 80 parts of ethanol, 1.68 parts of potassium hydroxide and 11 parts of water was stirred for 3 hours at reflux temperature. After evaporation, 100 parts of water were added to the residue and the mixture was neutralized with 1.8 parts of a 0.03M acetic acid solution. After stirring, the precipitated product was filtered off, washed with 2-propanone and dried, yielding 4.3 parts (70.1%) of 5-[(1H-imidazol-1-yl)phenylmethyl]-1H-benzimidazole-2-thiol; mp. 260.1° C. (compound 225).

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation, 100 parts of water
  3. additionwere added to the residue
  4. stirringAfter stirring
  5. filtrationthe precipitated product was filtered off
  6. washwashed with 2-propanone
  7. customdried

Sources & evidence

ORD record
ord-31069ec393bb44bcbe13393a237f98f6
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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