Acetyl chloride → Ethyl 5-nitro-1,2-benzisothiazole-3-acetate

HRID 48994

Reaction equation

HRID 48994 reaction equation
C([CH:3]([C:9]1[C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[S:11][N:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#N.C(Cl)(=O)C>C(O)C.C(OCC)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]2[S:11][N:10]=[C:9]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:13]=2[CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 12607115Ethyl alpha-cyano-5-nitro-1,2-benziso-thiazole-3-acetate

Product 1

HCID 18314495Ethyl 5-nitro-1,2-benzisothiazole-3-acetateYield 17.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl α-cyano-5-nitro-1,2-benzisothiazole-3-acetate (6.67 g, 0.0229 mol) is added to a solution of acetyl chloride (67.0 mL) in ethanol. The reaction mixture is refluxed overnight, cooled, and filtered to remove solids. The resultant filtrate is concentrated in vacuo to obtain a brown semi-solid. A mixture of the semi-solid in diethyl ether is stirred for two hours and filtered to obtain a solid. The solid is washed with diethyl ether and air-dried to give the title product as yellow crystals (1.04 g, mp 91-92° C.).

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationThe resultant filtrate is concentrated in vacuo
  6. customto obtain a brown semi-solid
  7. filtrationfiltered
  8. customto obtain a solid
  9. washThe solid is washed with diethyl ether
  10. customair-dried

Sources & evidence

ORD record
ord-ac498fb1ab074601bb817b4c06e43537
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Linked notes

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