Hydrochloric Acid → 3-Acetyl-4-hydroxy-1lambda~6~-naphtho[2,1-e][1,2]thiazine-1,1(2H)-dione

HRID 1730573Notes

Reaction equation

HRID 1730573 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][C:13]3[C:18]([C:7]=2[S:6]1(=[O:20])=[O:19])=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:2]([CH3:4])=[O:3].[Na].Cl>C(O)C>[C:2]([C:1]1[NH:5][S:6](=[O:20])(=[O:19])[C:7]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:8]=2[C:9]=1[OH:10])(=[O:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 124227312-(2-Oxopropyl)-1H-1lambda~6~-naphtho[2,1-d][1,2]thiazole-1,1,3(2H)-trione

Product 1

HCID 124227323-Acetyl-4-hydroxy-1lambda~6~-naphtho[2,1-e][1,2]thiazine-1,1(2H)-dioneYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28.9 gm (1.0 mol) of 2-acetonyl-3-oxo-naphth[2,1-d]isothiazoline-1,1-dioxide were added to a solution of 4.7 gm (2.04 gm-atom) of sodium in 125 ml of ethanol at 30° C. The resulting mixture was kept at 55° C for 2 hours, while stirring, and was subsequently refluxed for 15 minutes. After cooling, the reaction mixture was acidified with 350 ml of aqueous 9% hydrochloric acid, and the solid product formed thereby was suction-filtered off and washed with ice-cold 50% ethanol. Recrystallization from ethanol yielded 15.6 gm (54% of theory) of 3-acetyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-1,1-dioxide, m.p. 191°-192° C.

Workup

  1. temperaturewas subsequently refluxed for 15 minutes
  2. temperatureAfter cooling
  3. customthe solid product formed
  4. filtrationthereby was suction-filtered off
  5. washwashed with ice-cold 50% ethanol
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0f50fbf3eeab4e39b73763392defeae6
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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