Sodium Hydroxide → HCID 86631507, compound

HRID 911862Notes

Reaction equation

HRID 911862 reaction equation
[OH-].[Na+].C([NH:11][C:12]([NH:14][C:15]1[C:20]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)=[CH:19][C:18]([Br:30])=[CH:17][N:16]=1)=[S:13])(=O)C1C=CC=CC=1>CO>[Br:30][C:18]1[CH:19]=[C:20]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[C:15]([NH:14][C:12]([NH2:11])=[S:13])=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86631506HCID 86631506, compound

Product 1

HCID 86631507HCID 86631507, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Added 3 M aqueous sodium hydroxide (4.41 mL, 13.2 mmol) to a mixture of 1-benzoyl-3-(5-bromo-3-(4-cyanophenoxy)pyridin-2-yl)thiourea (3.00 g, 6.62 mmol) and MeOH (50 mL) and heated to 50° C. for 2 hours. Cooled, partitioned between ethyl acetate and water, washed twice with water, brine, dried, and concentrated. Added ethyl acetate (6 mL), heated to try to afford a solution. Added hexanes (8 mL) slowly, and cooled and triturated for 15 minutes. Filtered, to afford the title compound a (1.70 g, 73.6% yield) as a white solid.

Workup

  1. temperatureCooled
  2. custompartitioned between ethyl acetate and water
  3. washwashed twice with water, brine
  4. customdried
  5. concentrationconcentrated
  6. temperatureAdded ethyl acetate (6 mL), heated
  7. customto afford a solution
  8. customtriturated for 15 minutes
  9. filtrationFiltered

Sources & evidence

ORD record
ord-6db12bc85b044c04aa4570736d57929d
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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