Acetyl chloride → HCID 18519021, compound

HRID 1018677Notes

Reaction equation

HRID 1018677 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH:5]1[C:10]2[S:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[C:8]([C:16]([NH2:18])=[O:17])=[CH:7][CH:6]=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([C:6]1[CH:5]=[C:10]([S:11][CH2:12][CH2:13][CH2:14][Cl:1])[C:9]([OH:15])=[C:8]([CH:7]=1)[C:16]([NH2:18])=[O:17])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 53682000HCID 53682000, compound

Product 1

HCID 18519021HCID 18519021, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Solid aluminum chloride (9.0 g, 67.7 mmol) was suspended in 20 mL of dry dichloromethane at 0° C. The 7,8-dihydro-6H-5-oxa-9-thia-benzocycloheptene-4-carboxylic acid amide (2.7 g, 12.7 mmol) was added as a solution in 20 mL dichloromethane. The deep green solution was stirred at 0° C. for 10 min, then neat acetyl chloride (10 mL, 140.6 mmol) was added dropwise with stirring. The suspension was stirred at 0° C. for 20 min, then at rt for 30 h. The reaction was quenched with 4 N HCl and extracted repeatedly with ethyl acetate. Drying over Na2SO4 and concentration yeilded the crude product. Sgc (ethyl acetate) yielded the product as a tan solid (1.6 g, 44%). MS [M−H]− 286.

Workup

  1. stirringwith stirring
  2. stirringThe suspension was stirred at 0° C. for 20 min
  3. waitat rt for 30 h
  4. customThe reaction was quenched with 4 N HCl
  5. extractionextracted repeatedly with ethyl acetate
  6. dry with materialDrying over Na2SO4 and concentration

Sources & evidence

ORD record
ord-45e81c0c9c7545cdb07a2ec3822f06f9
Source dataset
uspto-grants-2002_11
Patent number
US06482852B2

Reaction notes

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