Dimethyl Sulfoxide → HCID 136338262, compound

HRID 1748979Notes

Reaction equation

HRID 1748979 reaction equation
CS(C)=O.[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[CH:9]=O.[NH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[SH:23].C(OCC)(=O)C>O>[Br:5][C:6]1[CH:7]=[C:8]([C:9]2[S:23][C:17]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=3[N:15]=2)[CH:11]=[CH:12][C:13]=1[OH:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 120002-Amino-4-chlorobenzenethiolHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 136338262HCID 136338262, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a dimethyl sulfoxide (DMSO) (2 mL) solvent, a solution including 3-bromo-4-hydroxybenzaldehyde (163.7 mg, 0.81 mmol) and 2-amino-4-chlorobenzenethiol (100 mg, 0.45 mmol) was refluxed for 1 hour. After cooling, the residual was distributed between ethyl acetate and water, and an organic layer was dried by using MgSO4, filtered, and evaporated under reduced pressure. The resultant residual was added to water, and then, the precipitate was filtered and the filtered product was washed with water and methylene chloride to obtain a solid Compound 95 (46.4 mg, 17.6%).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customan organic layer was dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. additionThe resultant residual was added to water
  7. filtrationthe precipitate was filtered
  8. washthe filtered product was washed with water and methylene chloride

Sources & evidence

ORD record
ord-acf11225a9a14715bc66163e434c3f84
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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