Acetic Anhydride → HCID 20426900, compound

HRID 615701Notes

Reaction equation

HRID 615701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:24])[N:10]([CH2:22][OH:23])[CH:11]=[C:12]3[C:17]=2[NH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13]3)=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:24])[N:10]([CH2:22][O:23][C:25](=[O:27])[CH3:26])[CH:11]=[C:12]3[C:17]=2[NH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20426898HCID 20426898, compound

Product 1

HCID 20426900HCID 20426900, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1.0 g. of 4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (2.8 mmol.) in 8 ml. of pyridine was added 4 ml. of acetic anhydride (42.3 mmol.), and the resulting suspension was stirred at room temperature for about 1 hour. The resulting solution was then concentrated under a nitrogen atmosphere, and the residue was titurated with methanol to yield a yellow precipitate which was washed with methanol and then air-dried to yield 4-(4-chlorophenyl)-2-[(acetyloxy)methyl]-5H-pyrido[3,4-b][1,4]-benzothiazin-3(2H)-one as a yellow solid (0.65 g; 58% yield) having the structural formula, ##STR12## a melting point in the range of 119°-120° C. and the following elemental analysis:

Workup

  1. concentrationThe resulting solution was then concentrated under a nitrogen atmosphere
  2. customto yield a yellow precipitate which
  3. washwas washed with methanol
  4. customair-dried

Sources & evidence

ORD record
ord-108a8a148e4f4d4584d5a39732837b62
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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