Sodium Hydroxide → HCID 59425700, compound

HRID 907193Notes

Reaction equation

HRID 907193 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) was stirred at room temperature as sodium hydroxide (31 mg, 0.78 mmol) was added. The reaction mixture was heated to 50° C. for 17 h. The reaction mixture was concentrated to remove methyl alcohol. Water was added to the mixture and the solid was 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. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customto remove methyl alcohol
  4. additionWater was added to the mixture
  5. filtrationthe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-03799885cf63496a918b68256aefdbf6
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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