Water → 2-benzyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

HRID 1730579Notes

Reaction equation

HRID 1730579 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 547193904-hydroxy-2H-naphtho[2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 681420442-benzyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.7 gm (0.035 mol of 4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide and 15.0 gm (0.0875 mol) of freshly distilled benzyl bromide were added to a mixture of 33 ml of water and 120ml of ethanol, and then 38.5 ml of 1 N sodium hydroxide were added dropwise. After stirring for 24 hours at room temperature, the crystals which had formed were suction-filtered off, washed with water and dried. Recrystallization from ethylene chloride/petroleum ether yielded 11.9 gm (86% of theory) of 2-benzyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide, m.p. 254°-156° C.

Workup

  1. customthe crystals which had formed
  2. filtrationwere suction-filtered off
  3. washwashed with water
  4. customdried
  5. customRecrystallization from ethylene chloride/petroleum ether

Sources & evidence

ORD record
ord-23eebf7a83f4456ba04eae9ca322433f
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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