Toluene → HCID 87217357, compound

HRID 1514894Notes

Reaction equation

HRID 1514894 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.C1(C)C=CC=CC=1.O=S(Cl)[Cl:30]>CN(C=O)C>[ClH:30].[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([Cl:30])=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 57786580HCID 57786580, compound

Product 1

HCID 87217357HCID 87217357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a mixture of 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (8.0 g) in SOCl2 (30 mL) was added 5 drops of DMF. After the suspension was stirred for 18 h, toluene (20 mL) was added and mixture was stirred for an additional 1 h. The suspension was filtered, washed with toluene and CH2Cl2. The white solid was dried under reduced pressure give 2-(2,6-dimethyl-phenyl)-3H-benzoimidazole-5-carbonyl chloride HCl salt; MS (ESI)m/z 267 (M+H).

Workup

  1. stirringmixture was stirred for an additional 1 h
  2. filtrationThe suspension was filtered
  3. washwashed with toluene and CH2Cl2
  4. customThe white solid was dried under reduced pressure

Sources & evidence

ORD record
ord-96b0e143d34741849de67e374bc02469
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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