4-Toluenesulfonyl chloride → HCID 178431886, compound

HRID 243521Notes

Reaction equation

HRID 243521 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:17]([CH3:18])=[CH:16][S:15][CH:14]=1)=S.NC1C=C(F)C=CC=1NC(NC1C(C)=CSC=1)=S.[OH-].[Na+].C1(C)C=CC(S([Cl:48])(=O)=O)=CC=1>C1COCC1.O>[ClH:48].[F:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:10]([NH:12][C:13]3[C:17]([CH3:18])=[CH:16][S:15][CH:14]=3)=[N:9][C:3]=2[CH:4]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 22139847HCID 22139847, compoundHCID 86011843HCID 86011843, compound

Product 1

HCID 178431886HCID 178431886, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The mixture of 1-(2-amino-5-fluorophenyl)-3-(4-methylthiophen-3-yl)thiourea and 1-(2-amino-4-fluorophenyl)-3-(4-methylthiophen-3-yl)thiourea (1.75 g) was dissolved in THF (50 ml) and admixed with a solution of sodium hydroxide (0.622 g) and water (15 ml). Within 5 min, a solution of p-toluenesulfonyl chloride (1.304 g) and THF (10 ml) was added dropwise. On completion of addition, the mixture was stirred at room temperature for a half hour. The reaction mixture was poured onto water, and the aqueous phase was extracted three times. The combined ether phases were dried with magnesium sulfate, filtered and concentrated. The crude product was dissolved in ethyl acetate and adjusted to pH 2 using ethereal HCl. It was precipitated by adding ether. After drying, 750 mg of the desired product were obtained.

Workup

  1. additionOn completion of addition
  2. additionThe reaction mixture was poured onto water
  3. extractionthe aqueous phase was extracted three times
  4. dry with materialThe combined ether phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude product was dissolved in ethyl acetate
  8. customIt was precipitated
  9. additionby adding ether
  10. customAfter drying

Sources & evidence

ORD record
ord-dd4b4ee3528241658d09238314deae25
Source dataset
uspto-grants-2014_02
Patent number
US08653259B2

Reaction notes

Loading…