Hydrochloric Acid → HCID 13653165, compound

HRID 1380912Notes

Reaction equation

HRID 1380912 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[N:12]([CH2:15][C:16]([OH:18])=[O:17])[C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].Cl>N1C=CC=CC=1>[C:23]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:13](=[O:14])[N:12]([CH2:15][C:16]([OH:18])=[O:17])[C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[S:9]2)=[CH:6][CH:7]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 13653157HCID 13653157, compound

Product 1

HCID 13653165HCID 13653165, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of [3,4-dihydro-2-(4-hydroxyphenyl)-3-oxo-2H-1,4-benzothiazin-4-yl]acetic acid (compound No. 17, 49.2 g) in pyridine (150 ml), acetic anhydride (22 ml) is added and the mixture is standed overnight. The reaction mixture is poured into a mixture of 6N HCl and ice, and the separated oil is extracted with ethyl acetate. The organic layer is washed with N HCl, dried over anhydrous sodium sulfate and concentrated in vacuo. Benzene and ether are added to the residue and separated crystals are collected by filtration to give 34.9 g (63%) of the titled compound.

Workup

  1. extractionthe separated oil is extracted with ethyl acetate
  2. washThe organic layer is washed with N HCl
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. additionBenzene and ether are added to the residue
  6. customseparated crystals
  7. filtrationare collected by filtration

Sources & evidence

ORD record
ord-345c4f922c07467fb9a10c27ade6f33e
Source dataset
uspto-grants-1986_04
Patent number
US04584300

Reaction notes

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