Ethyl Acetate → HCID 18412288, compound

HRID 2288478Notes

Reaction equation

HRID 2288478 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[C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37](C)[CH:36]=1.[C:44](OCC)(=O)C>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][CH2:44][C:35]4[CH:36]=[CH:37][C:38]([C:39]#[N:40])=[CH:41][CH:42]=4)=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1442674-Bromo-2-methylbenzonitrileHCID 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-mercapto-benzimidazol-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-bromo-methylbenzonitrile 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 sulphate. 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 sulphate
  4. filtrationAfter filtration and distillation of the solvent the desired compound
  5. customwas obtained as a beige-white solid

Sources & evidence

ORD record
ord-5047e8f7c5f544a5909583388412537c
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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