Ammonia → 4-Isopropoxy-3-thioureidobenzenesulfonamide

HRID 405674Notes

Reaction equation

HRID 405674 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[N:15]=[C:16]=[S:17])([CH3:3])[CH3:2].[NH3:18]>CO>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[NH:15][C:16]([NH2:18])=[S:17])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866653704-Isopropoxy-3-isothiocyanato-benzenesulfonamide

Product 1

HCID 866655834-Isopropoxy-3-thioureidobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 4-isopropoxy-3-isothiocyanato-benzenesulfonamide (17.8 g, 65.2 mmol, example 2, step e) was treated with a 2 M solution of ammonia in MeOH (250 mL) and the resulting solution was stirred at room temperature for 18 h. The reaction mixture was then concentrated to about half the volume until a large amount of tan solid precipitated. The suspension was cooled to 0° C. for 30 minutes and was filtered. The solid was washed with methanol and ether to give the title compound as a cream colored solid.

Workup

  1. concentrationThe reaction mixture was then concentrated to about half the volume until a large amount of tan solid
  2. customprecipitated
  3. temperatureThe suspension was cooled to 0° C. for 30 minutes
  4. filtrationwas filtered
  5. washThe solid was washed with methanol and ether

Sources & evidence

ORD record
ord-0f5602def9e44f86b5b52862fec149a9
Source dataset
uspto-grants-2014_06
Patent number
US08753857B2

Reaction notes

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