Chloroacetaldehyde → N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamide

HRID 1035831Notes

Reaction equation

HRID 1035831 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)[C:2]([NH2:4])=[S:3].Cl[CH2:17][CH:18]=O>C(O)C>[S:3]1[CH:18]=[CH:17][N:4]=[C:2]1[NH:1][C:5]1[CH:6]=[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 86674185N-(3-thioureidophenyl)methanesulfonamide

Product 1

HCID 86674184N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamideYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-thioureidophenyl)methanesulfonamide 54 (1.14 g, 4.65 mmol) and 50% aq. chloroacetaldehyde solution (3.65 mL, 23.25 mmol) were taken into ethanol and refluxed for 2 hours. Reaction mixture was concentrated and aq. Saturated NaHCO3 was added. Resulting light brown solid was filtered and washed with water, dried under high vacuum to obtain N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamide 55 (1.17 g, 93% yield). Resulting product was further used without further purification. MS (ES) m/z 270 (M+H+).

Workup

  1. temperaturerefluxed for 2 hours
  2. customReaction mixture
  3. concentrationwas concentrated
  4. additionaq. Saturated NaHCO3 was added
  5. customResulting light brown solid
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-decce2a17b204d4fa75e7d5ccb75194b
Source dataset
uspto-grants-2013_10
Patent number
US08546400B2

Reaction notes

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