Acetic Anhydride → 2-Acetamido-5-(4-nitrobenzyl)-4-propylthiazole

HRID 1613246Notes

Reaction equation

HRID 1613246 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[C:5]([CH2:7][CH2:8][CH3:9])[N:6]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>CN(C)C1C=CN=CC=1>[C:20]([NH:1][C:2]1[S:3][C:4]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[C:5]([CH2:7][CH2:8][CH3:9])[N:6]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 197755452-Amino-5-(4-nitrobenzyl)-4-propylthiazole

Product 1

HCID 197755582-Acetamido-5-(4-nitrobenzyl)-4-propylthiazole

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

2 g (7.2 mmol) of 2-amino-5-(4-nitrobenzyl)-4-propylthiazole in 2.5 ml of acetic anhydride, in the presence of 88 mg of 4-dimethylaminopyridine (0.72 mmol), are heated at 80° C. for 1 hour. As the reaction mixture is cooled, the formation of a precipitate is observed. This is filtered off and washed with ether to give 1.6 g of the derivative 2-acetamido-5-(4-nitrobenzyl)-4-propylthiazole, which is pale yellow solid melting at 170° C.

Workup

  1. temperatureAs the reaction mixture is cooled
  2. filtrationThis is filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-99b661cd7b664243a7b59ff01b96cc47
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

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