Dimethylformamide → 5-Chloro-2-(3-nitro-phenyl)-thiazole

HRID 2262748Notes

Reaction equation

HRID 2262748 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN(C=O)C.S(Cl)([Cl:23])(=O)=O>C(Cl)(Cl)Cl>[Cl:23][C:12]1[S:11][C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24648Sulfuryl chlorideHCID 118058602-(3-Nitrophenyl)-1,3-thiazole

Product 1

HCID 575722385-Chloro-2-(3-nitro-phenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2-(3-nitro-phenyl)-thiazole (18.5 g, 89.7 mmol) in a mixture of chloroform (150 ml) and anhydrous DMF (40 ml) was slowly added sulfuryl chloride (28.2 ml, 359 mmol). After the addition, the resultant mixture was stirred at reflux for 3 hours. The cooled mixture was concentrated under reduced pressure and the residue was partitioned between aqueous calcium chloride (3M) and ethyl acetate. The organic layer was washed with aqueous sodium carbonate, dried over magnesium sulphate and evaporated to dryness to leave the desired product. 20.6 g (80%).

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 3 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between aqueous calcium chloride (3M) and ethyl acetate
  5. washThe organic layer was washed with aqueous sodium carbonate
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c76962c236c64a53adcfb2bd85695e6f
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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