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

HRID 537879Notes

Reaction equation

HRID 537879 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-22d29d370b464ea9be57fe2479bb1a6e
Source dataset
uspto-grants-2014_10
Patent number
US08865709B2

Reaction notes

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