Acetic Anhydride → HCID 22401469, compound

HRID 260484Notes

Reaction equation

HRID 260484 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[CH:15][C:14]([Cl:27])=[CH:13][CH:12]=2)=[O:8].[C:31](OC(=O)C)(=[O:33])[CH3:32]>O1CCCC1.O>[C:31]([NH:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:20])=[CH:15][C:14]([Cl:27])=[CH:13][CH:12]=2)=[O:8])(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 483550HCID 483550, compound

Product 1

HCID 22401469HCID 22401469, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-aminobenzyl) 3-phenylsulfonyl-5-chloroindole-2-carboxamide (Examplle 41) (176 mg, 0.4 mmol) in dry tetrahydrofuran (7 mL) containing acetic anhydride (0.05 mL, 0.5 mmol) was stirred at room temperature for 16 hours. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered through charcoal, and the solvents evaporated. The residue was triturated with methylene chloride and the solid collected by filtration to give the product, mp 249°-250° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered through charcoal
  4. customthe solvents evaporated
  5. customThe residue was triturated with methylene chloride
  6. filtrationthe solid collected by filtration
  7. customto give the product, mp 249°-250° C.

Sources & evidence

ORD record
ord-453cf328b21945fd85e996151740ad71
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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