Acetic Anhydride → N-(5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide

HRID 595081Notes

Reaction equation

HRID 595081 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][C:8]([CH3:13])([CH3:12])[CH2:7][C:5]=2[N:6]=1.[CH3:14][C:15](OC(C)=O)=[O:16]>>[CH3:12][C:8]1([CH3:13])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:15](=[O:16])[CH3:14])[S:3][C:4]=2[C:10](=[O:11])[CH2:9]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 5878742-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one

Product 1

HCID 2829723N-(5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamideYield 75%

Procedure

2-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one (40.5 g, 0.206 mol) and Ac2O (400 mL) are heated at 100° C. for 4 h. After cooling to RT, the reaction mixture is concentrated in vacuo. The precipitated solid is collected by filtration and affords N-(5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide (36.5 g, 75% yield).

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. filtrationThe precipitated solid is collected by filtration

Sources & evidence

ORD record
ord-9e0b3ed214c44b6f9585885bc0ad7a60
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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