4-Toluenesulfonyl chloride → HCID 67457973, compound

HRID 469803Notes

Reaction equation

HRID 469803 reaction equation
[Br:1][C:2]1[C:3]([OH:24])=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=S)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[C:3]2[O:24][C:9]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 86637871HCID 86637871, compound

Product 1

HCID 67457973HCID 67457973, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.798 mg (1.93 mmol) 1-(3-bromo-2-hydroxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-thiourea in 8 ml THF, 0.197 g (4.8 mmol) NaOH (in 5 ml water) and 0.419 g (2.12 mmol) toluene-4-sulfonyl chloride are added. The reaction mixture is stirred at room temperature for 1.5 h. Then the reaction mixture is concentrated in vacuo. To the residue EtOAc and sat. NaCl-solution are added and the layers are separate. The water layer is extracted 3× with EtOAc. The combined organic layers are washed with water, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is stirred in diethyl ether, filtered and dried to afford the title compound.

Workup

  1. additionare added
  2. concentrationThen the reaction mixture is concentrated in vacuo
  3. additionTo the residue EtOAc and sat. NaCl-solution are added
  4. customthe layers are separate
  5. extractionThe water layer is extracted 3× with EtOAc
  6. washThe combined organic layers are washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. stirringThe residue is stirred in diethyl ether
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-7714daa139954549afc0caaf84d13fd8
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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