Benzoyl chloride → HCID 18399622, compound

HRID 381281Notes

Reaction equation

HRID 381281 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([C:13]1[S:14][CH:15]=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=1[OH:18])(=[O:12])[CH3:11]>CN(C)C1C=CN=CC=1.ClCCl>[C:10]([C:13]1[S:14][CH:15]=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=1[O:18][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 12520005HCID 12520005, compound

Product 1

HCID 18399622HCID 18399622, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3.48 mL of benzoyl chloride was added dropwise to a solution of 5.0 g of methyl 2-acetyl-3-hydroxythiophene-4-carboxylate (prepared as described in J. Chem. Soc. Perkin Trans I, 1986, 507) and 3.66 g of 4-dimethylaminopyridine in 100 mL of dichloromethane at 20-25° C. and stirred for 2 hours. The mixture was washed with 0.5N hydrochloric acid, water (2×20 mL), 2.5% aqueous sodium bicarbonate (2×40 mL) and water (2×20 mL). The organic layer was dried with sodium sulphate, evaporated to dryness in vacuo and purified by flash chromatography using chloroform/ethyl-acetate (100:1). The yield of Compound 1C was 7.089, as a yellow deliquescent solid, which was used in the next step without further purification.

Workup

  1. washThe mixture was washed with 0.5N hydrochloric acid, water (2×20 mL), 2.5% aqueous sodium bicarbonate (2×40 mL) and water (2×20 mL)
  2. dry with materialThe organic layer was dried with sodium sulphate
  3. customevaporated to dryness in vacuo
  4. custompurified by flash chromatography
  5. customas a yellow deliquescent solid, which was used in the next step without further purification

Sources & evidence

ORD record
ord-de606e4db0d04f28a4f86d9f4a0e0e73
Source dataset
uspto-grants-2001_10
Patent number
US06306861B1

Reaction notes

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