Acetic Anhydride → HCID 20143056, compound

HRID 649326Notes

Reaction equation

HRID 649326 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:20][CH3:21])[C:13](=[O:14])[N:12]([CH3:15])[C:11]3[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[C:22](OCC)(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+].[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[C:22]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:20][CH2:21][C:33](=[O:35])[CH3:34])[C:13](=[O:14])[N:12]([CH3:15])[C:11]3[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=3[S:9]2)=[CH:6][CH:7]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 20143016HCID 20143016, compound

Product 1

HCID 20143056HCID 20143056, compoundYield 85.7%

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 3,4-dihydro-2-(4-hydroxyphenyl)-4-methyl-2-methylamino-3-oxo-2H-1,4-benzothiazine (3.0 g, compound No. 66) in acetic anhydride (14.3 ml), fused sodium acetate (3.3 g) is added. The mixture is stirred for 3.5 hours at 85° C. and then poured into a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution. The separated crystals are collected by filtration to give 3.3 g (85.7%) of the title compound.

Workup

  1. filtrationThe separated crystals are collected by filtration

Sources & evidence

ORD record
ord-a7091e945d6f440996861e8f4c5cd07e
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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