Dimethyl Sulfoxide → HCID 54336684, compound

HRID 1648313Notes

Reaction equation

HRID 1648313 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.CS(C)=O.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][CH2:21][CH2:22][OH:23])[C:14]=2[N:13]=[CH:12]1.O>C(Cl)Cl>[CH2:15]([N:11]([CH2:12][CH2:1][CH3:2])[CH:20]([C:19]1[C:14]2[N:13]=[CH:12][NH:11][C:15]=2[CH:16]=[CH:17][CH:18]=1)[CH2:21][CH:22]=[O:23])[CH2:14][CH3:19]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 19919336HCID 19919336, compound

Product 1

HCID 54336684HCID 54336684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (1.2 mL, 0.014 mol) was added with stirring to methylene chloride (20mL) at -78° C. Ten minutes after addition was complete, DMSO (2 mL) was added and stirring was continued for an additional 10 minutes. β-Dipropylamino)-1H-benzimidazole-4propanol (2.1 g, 7.5 mmol) in methylene chloride was added and, after 30 minutes, the solution was allowed to warm to room temperature. Water was added, the methylene chloride was separated and evaporated, and the residue was chromatographed on silica gel to give β-(dipropylamino)-1H-benzimidazole-4-propanal as an oil.

Workup

  1. additionTen minutes after addition
  2. customthe methylene chloride was separated
  3. customevaporated
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b0fca06c77f14df395f9ec033ac19276
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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