Water → HCID 24877383, compound

HRID 2196174Notes

Reaction equation

HRID 2196174 reaction equation
[CH3:1][C:2]1([CH3:34])[O:6]/[C:5](=[C:7]2/[C:8](=[O:27])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([S:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])[CH:11]=3)/[CH:4]=[C:3]1[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[OH-].[Na+].O>CO>[CH3:1][C:2]1([CH3:34])[O:6]/[C:5](=[C:7]2/[C:8](=[O:27])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([S:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])[CH:11]=3)/[CH:4]=[C:3]1[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 16654977HCID 16654977, compound

Product 1

HCID 24877383HCID 24877383, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
66 °C

Procedure

A mixture of methyl 2-{[(3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]thio}benzoate (50 mg) and 1M NaOH (3 mL) in 20 mL of MeOH was heated in 66° C. bath for 2 hours. The mixture was cooled to room temp, poured into 100 mL of water, and acidified to about pH 3. The precipitates were filtered, washed with water and dried in vacuo to give 2-{[(3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]thio}benzoic acid as a brown solid. Yield: 50 mg, 97%.

Workup

  1. temperatureThe mixture was cooled to room temp
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5c0d3b33487f425ca6f41dba45013064
Source dataset
uspto-grants-2012_12
Patent number
US08338415B2

Reaction notes

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