Triethylamine → HCID 21273507, compound

HRID 1382933Notes

Reaction equation

HRID 1382933 reaction equation
ClC(OCCCC)=O.[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]=1[CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1.[CH2:28]([N:30](CC)CC)C.Cl.CN>CN(C)C=O.O>[CH3:28][NH:30][C:23](=[O:25])[C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:10]2[NH:9][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 61140Butyl chloroformateHCID 6364545Methylamine hydrochlorideHCID 190232394-((1H-benzo[d]imidazol-2-yl)methyl)benzoic acid

Product 1

HCID 21273507HCID 21273507, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2.8 ml of butyl chloroformate are added dropwise at -5° to a solution of 5.0 g (0.020 mol) of p-[(2-benzimidazolyl)methyl]benzoic acid and 2.8 ml (0.020 mol) of triethylamine in 68 ml of dimethylformamide. After stirring at 0°-5° for 30 minutes 1.32 g (0.020 mol) of methylamine hydrochloride and 2.8 ml (0.020 mol) of triethylamine in 28 ml of dimethylformamide and 1.4 ml of water are added. The temperature is then left to rise to room temperature and the mixture is stirred for a further 18 hours. After concentration under reduced pressure the residue is chromatographed on 400 g of silica gel with chloroform/ethanol (4:1) as the elution agent. The uniform fractions give 2.0 g (38%) of N-methyl-p-[(2-benzimidazolyl)methyl]benzamide, m.p. 250°-255° (dec.), as a colourless powder.

Workup

  1. additionare added
  2. waitThe temperature is then left
  3. customto rise to room temperature
  4. concentrationAfter concentration under reduced pressure the residue
  5. customis chromatographed on 400 g of silica gel with chloroform/ethanol (4:1) as the elution agent

Sources & evidence

ORD record
ord-f4246d7edcf7421b8b20ed0209725102
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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