Water → HCID 86640674, compound

HRID 1919561Notes

Reaction equation

HRID 1919561 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([NH2:12])=O)[N:9]=1)(=[O:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(OCC)(=O)C.O>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]#[N:12])[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl Acetate2×HCID 2572002-Acetylaminothiazol-4-carboxamide

Product 1

HCID 86640674HCID 86640674, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.1 g (27.5 mmol) 2-Acetylaminothiazol-4-carboxamide was dispersed in 27 ml pyridine, and 10.5 g (55 mmol) p-tolylsulfonyl chloride was added, to carry out reaction at room temperature for 10 hr, and then 150 ml ethyl acetate and 100 ml water were added to separate the layers. The resultant organic phase was washed with diluted HCl till aqueous phase being acidic, and then washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 3.45 g 2-acetylamino-4-cyanothiazole (yield 75%) with mp 185-188° C. (ethyl acetate). 1H NMR (DMSO-d6) 2.18 (3H, s); 8.33 (1H, s); 12.55 (1H, s).

Workup

  1. customreaction at room temperature for 10 hr
  2. customto separate the layers
  3. washThe resultant organic phase was washed with diluted HCl till aqueous phase
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d88d0e3957648158b3b5345d7724067
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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