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

HRID 1949878Notes

Reaction equation

HRID 1949878 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-cef517fd516e4862a0c59aa08ab6c8db
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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