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

HRID 628031

Reaction equation

HRID 628031 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-4440b6d165154b938c44dc28a91b72f9
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Linked notes

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