Benzoyl chloride → HCID 44599946, compound

HRID 1876905Notes

Reaction equation

HRID 1876905 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][C:10]2=[NH:14])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][C:10]2=[N:14][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 98593863-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinimine

Product 1

HCID 44599946HCID 44599946, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-(2-Chloro-5-pyridinylmethyl)-2-iminothiazolidine (227 mg, 1.1 mmol) and triethylamine (110 mg, 1.1 mmol) were dissolved in 10 ml of acetonitrile, into which, benzoyl chloride (141 mg, 1.0 mmol) dissolved in acetonitrile 5 ml was added under cooling with ice, and stirred at room temperature overnight. After distilling the solvent off under reduced pressure followed by extraction with ethyl acetate, the ethyl acetate layer was washed with 2N-hydrochloric acid, saturated aqueous sodium bicarbonate, and water in this order, and the ethyl acetate layer was dehydrated and dried, and then the ethyl acetate layer was distilled off, and remaining oil was purified by a silica gel column chromatography to obtain the intended substance. The crude crystal of the intended substance was washed with hexane. Yield: 160 mg (65%). Melting point: 133° C.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. distillationAfter distilling the solvent off under reduced pressure
  4. extractionfollowed by extraction with ethyl acetate
  5. washthe ethyl acetate layer was washed with 2N-hydrochloric acid, saturated aqueous sodium bicarbonate, and water in this order
  6. customdried
  7. distillationthe ethyl acetate layer was distilled off
  8. customwas purified by a silica gel column chromatography
  9. customto obtain the intended substance
  10. washThe crude crystal of the intended substance was washed with hexane

Sources & evidence

ORD record
ord-00c2f908c5a44f7ab99dc6e28d082001
Source dataset
uspto-grants-2012_11
Patent number
US08309733B2

Reaction notes

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