Sodium Hydroxide → HCID 10046967, compound

HRID 723965Notes

Reaction equation

HRID 723965 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:31]=[CH:30][C:16]2[N:17]=[C:18]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)[S:19][C:15]=2[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>O1CCCC1>[Br:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][NH:20][C:18]2[S:19][C:15]3[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:31]=[CH:30][C:16]=3[N:17]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10414012HCID 10414012, compound

Product 1

HCID 10046967HCID 10046967, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzoyl-3-{2-[2-(4-bromo-phenyl)-ethylamino]-benzothiazol-6-yl}-thiourea (Example 38, 71.1 mg, 0.139 mmol) was dissolved in tetrahydrofuran (3 mL). Aqueous NaOH (2M, 0.3 mL) was added and the mixture refluxed under argon for 44 hours. The mixture was cooled to room temperature and the solvent evaporated. Water (2 mL) and ethyl acetate (10 mL) were added and the layers separated. The aqueous phase was saturated with NaCl before extraction. An additional 10 mL of ethyl acetate was added and the layers separated. The combined extracts were dried over MgSO4, filtered and evaporated to give a yellow solid (51.3 mg, 91%).

Workup

  1. temperaturethe mixture refluxed under argon for 44 hours
  2. customthe solvent evaporated
  3. additionWater (2 mL) and ethyl acetate (10 mL) were added
  4. customthe layers separated
  5. extractionThe aqueous phase was saturated with NaCl before extraction
  6. additionAn additional 10 mL of ethyl acetate was added
  7. customthe layers separated
  8. dry with materialThe combined extracts were dried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-75372c9ff3aa45368612da1e946375e7
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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