Sodium Hydroxide → HCID 59425700, compound

HRID 1009626Notes

Reaction equation

HRID 1009626 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:20]([CH2:32][CH3:33])[C:21]3[C:26]([C:27]=2[C:28]#[N:29])=[CH:25][CH:24]=[C:23]([O:30][CH3:31])[CH:22]=3)[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO.O>[C:28]([C:27]1[C:26]2[C:21](=[CH:22][C:23]([O:30][CH3:31])=[CH:24][CH:25]=2)[N:20]([CH2:32][CH3:33])[C:19]=1[C:15]1[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:18]=[CH:17][CH:16]=1)#[N:29]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59426163HCID 59426163, compound

Product 1

HCID 59425700HCID 59425700, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-benzoyl-3-[3-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-thiourea (241 mg, 0.530 mmol) in methyl alcohol (2.0 ml) and water (0.5 mL) is stirred at room temperature as sodium hydroxide (31 mg, 0.78 mmol) is added. The reaction mixture is heated to 50° C. for 17 h. The reaction mixture is concentrated to remove methyl alcohol. Water is added to the mixture and the solid is filtered, washed with water and dried to give 179 mg of [3-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-thiourea, compound 767 (96% yield) as a white solid.

Workup

  1. additionis added
  2. concentrationThe reaction mixture is concentrated
  3. customto remove methyl alcohol
  4. additionWater is added to the mixture
  5. filtrationthe solid is filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-529bbe9dbd6142ac9d23924593dd4512
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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