Acetic Anhydride → N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamide

HRID 1766300Notes

Reaction equation

HRID 1766300 reaction equation
[C:1]([N:4]([C:8]1[C:12]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].NC1C2C=C([N+]([O-])=O)C=CC=2SN=1.C(OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C=O)C>[C:1]([N:4]([C:8]1[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1)[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1586383-Amino-5-nitrobenzisothiazoleHCID 21110339N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide

Product 1

HCID 21110338N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide (KRB01049): To a solution of 3-amino-5-nitrobenzisothiazole (1.00 g, 5.12 mmol) in DMF (20 mL) was added acetic anhydride (1 mL) and triethylamine (1 mL) and the resulting solution was stirred for 4 h. The yellow precipitate was filtered, washed quickly with cold ethyl acetate, and dried in vacuo (1.139 g, 80%). 1H NMR (CDCl3): δ 9.20 (1H, d, J=2.5 Hz), 8.87 (1H, d, J=9.4 Hz), 8.55 (1H, dd, J=9.4, 2.5 Hz), 2.69 (3H, s), 2.63 (3H, s).

Workup

  1. filtrationThe yellow precipitate was filtered
  2. washwashed quickly with cold ethyl acetate
  3. customdried in vacuo (1.139 g, 80%)

Sources & evidence

ORD record
ord-3f0ccfe3275b4fee9ba9d415fcb41969
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

Loading…