Water → HCID 24877383, compound

HRID 333404Notes

Reaction equation

HRID 333404 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-a848ab58cbfe424890254ed06a7b19c3
Source dataset
uspto-grants-2014_11
Patent number
US08877923B2

Reaction notes

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