Water → 4,5-Dihydro-6-oxa-1-thia-3-aza-benzo[e]azulene-2-carboxylic acid

HRID 84615Notes

Reaction equation

HRID 84615 reaction equation
C([O:3][C:4]([C:6]1[S:15][C:14]2[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[O:11][CH2:10][CH2:9][C:8]=2[N:7]=1)=[O:5])C.[OH-].[Na+].O>C1COCC1>[S:15]1[C:14]2[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[O:11][CH2:10][CH2:9][C:8]=2[N:7]=[C:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 579000864,5-Dihydro-6-oxa-1-thia-3-aza-benzo[e]azulene-2-carboxylic acid ethyl ester

Product 1

HCID 866348484,5-Dihydro-6-oxa-1-thia-3-aza-benzo[e]azulene-2-carboxylic acidYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,5-dihydro-6-oxa-1-thia-3-aza-benzo[e]azulene-2-carboxylic acid ethyl ester (1 eq, 1.9 mmol, 530 mg), and sodium hydroxide (5 eq, 9.6 mmol, 385 mg), in THF (5 ml) and water (5 ml) was allowed to stir at RT for 3 hrs. Reaction concentrated in vacuo and the solid washed with water to give 4,5-dihydro-6-oxa-1-thia-3-aza-benzo[e]azulene-2-carboxylic acid (290 mg, yield 58%).

Workup

  1. customReaction
  2. concentrationconcentrated in vacuo
  3. washthe solid washed with water

Sources & evidence

ORD record
ord-a0efd4df66c642e6b20e944cd9bba209
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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