Butyryl chloride → HCID 25188324, compound

HRID 1896777Notes

Reaction equation

HRID 1896777 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.[C:18](Cl)(=[O:22])[CH2:19][CH2:20][CH3:21].C(OCC)(=O)C>N1C=CC=CC=1>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([C:7]2[S:8][C:9]3[CH:15]=[CH:14][C:13]([NH:16][C:18](=[O:22])[CH2:19][CH2:20][CH3:21])=[CH:12][C:10]=3[N:11]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 673310502-p-Tolylbenzo[d]thiazol-5-amine

Product 1

HCID 25188324HCID 25188324, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-p-tolylbenzo[d]thiazol-5-amine (110 mg, 0.46 mmol) in pyridine (3 mL) at room temperature was added butyryl chloride (53 μL, 0.50 mmol). The resulting mixture was stirred at room temperature for 2 days. Ethyl acetate was added and the organic layer was washed with saturated aqueous copper sulfate, followed by aqueous sodium bicarbonate and finally with brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 50:50 v/v to afford 25 mg (18%) of the title compound (LCMS RT=7.10 min, MH+ 311.0)

Workup

  1. washthe organic layer was washed with saturated aqueous copper sulfate
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customevaporated
  4. customThe resulting solid was purified by column chromatography
  5. washeluting with ethyl acetate/hexanes 50:50 v/v

Sources & evidence

ORD record
ord-442731db3a82485c963e2c3fcba55436
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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