Potassium Carbonate → HCID 18412288, compound

HRID 50339Notes

Reaction equation

HRID 50339 reaction equation
[C:1]1([N:7]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:8]([C:10]2[CH:20]=[CH:19][C:13]3[N:14]([CH3:18])[C:15]([SH:17])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=1>C(O)C>[C:1]1([N:7]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:8]([C:10]2[CH:20]=[CH:19][C:13]3[N:14]([CH3:18])[C:15]([S:17][CH2:35][C:36]4[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 178472062HCID 178472062, compound

Product 1

HCID 18412288HCID 18412288, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1.30 g (3.4 mmol) of 1-methyl-2-mercaptobenzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide, 0.52 g (3.74 mmol) of potassium carbonate and 0.66 g (3.4 mmol) of 4-bromomethylbenzonitrile were dissolved in 40 mL of absolute ethanol, stirred for 4 hours at 60° C. and 16 hours at room temperature. Then the solvent was distilled off in vacuo, the crude product was taken up in 30 mL of methylene chloride, washed with 40 mL of water and dried with sodium sulfate. After filtration and distillation of the solvent, the desired compound was obtained as a beige-white solid. Yield: 1.8 g (100% of theory); Rf value: 0.64 (silica gel; ethyl acetate).

Workup

  1. distillationThen the solvent was distilled off in vacuo
  2. washwashed with 40 mL of water
  3. dry with materialdried with sodium sulfate
  4. filtrationAfter filtration and distillation of the solvent

Sources & evidence

ORD record
ord-6eac1ae2852d4994b97c9b4ea4ec76b4
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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