Acetic Anhydride → HCID 86604985, compound

HRID 15243Notes

Reaction equation

HRID 15243 reaction equation
[OH:1][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[NH2:9][C:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15][C:14]=2[CH:13]=[CH:12][CH:11]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1.O>[OH:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[C:23]([NH:9][C:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86604987HCID 86604987, compound

Product 1

HCID 86604985HCID 86604985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of the aminodibenzothiophene triflate (200 mg, 0.58 mmol) in pyridine (4.0 ml), was added acetic anhydride (0.29 ml, 2.88 mmol) dropwise. The reaction mixture was stirred at room temperature for 12 hours, diluted with water (20 ml), and extracted with ethyl acetate (3×10 ml). The combined organic layers were washed successively with water (2×20 ml), saturated aqueous sodium bicarbonate solution (1×20 ml) and brine (1×20 ml), dried (Na2SO4) and evaporated in vacuo. The residual solid was triturated with petrol to give the title compound (xii).

Workup

  1. extractionextracted with ethyl acetate (3×10 ml)
  2. washThe combined organic layers were washed successively with water (2×20 ml), saturated aqueous sodium bicarbonate solution (1×20 ml) and brine (1×20 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residual solid was triturated with petrol

Sources & evidence

ORD record
ord-721348e7c8d9472098fc923fffd92bd0
Source dataset
uspto-grants-2010_06
Patent number
US07732483B2

Reaction notes

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