Acetyl chloride → 7-Acetyl-4-methoxybenzo[d]thiazol-2(3H)-one

HRID 749238Notes

Reaction equation

HRID 749238 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:13]([C:6]1[C:7]2[S:11][C:10](=[O:12])[NH:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 127708784-Methoxy-2(3H)-benzothiazolone

Product 1

HCID 450769887-Acetyl-4-methoxybenzo[d]thiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methoxy-1,3-benzothiazol-2(3H)-one (DE 3017977 A1) (1.92 g) in dry dichloromethane (50 ml) was cooled to ˜5° C. under nitrogen. Acetyl chloride (1.43 ml) and aluminium chloride (3.43 g) were added in one portion, and stirred for 2 h at RT. The reaction was quenched carefully with water, followed by addition of 2N HCl and dichloromethane. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with brine and dried (Na2SO4) and evaporated in vacuo to give the title compound (1.92 g). LCMS RT=2.50 min

Workup

  1. customThe reaction was quenched carefully with water
  2. additionfollowed by addition of 2N HCl and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8ac670beee6d43589a1fc5b855c60a6b
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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