1,1'-Thiocarbonyldiimidazole → HCID 21254756, compound

HRID 636504Notes

Reaction equation

HRID 636504 reaction equation
[NH2:1][C:2]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][OH:8].[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22]>C(Cl)(Cl)Cl>[CH2:14]([O:13][C:12]1[C:2]2[NH:1][C:21](=[S:22])[N:4]([CH2:5][CH2:6][CH2:7][OH:8])[C:3]=2[CH:9]=[CH:10][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 21254653HCID 21254653, compound

Product 1

HCID 21254756HCID 21254756, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-amino-3-benzyloxy-N-(3-hydroxypropyl)aniline (100 mg) in chloroform (2 ml) was added 1,1′-thiocarbonyldiimidazole (72.7 mg) at ambient temperature, and the mixture was stirred for 2 hours at the same temperature and refluxed for 5 hours. The reaction mixture was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, v/v) to give 4-benzyloxy-1-(3-hydroxypropyl)-2-thioxo-2,3-dihydro-1H-benzimidazole (75 mg).

Workup

  1. temperaturerefluxed for 5 hours
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-ec30aa24d1af4f6a9af52b9c3d13926a
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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