Acetic Anhydride → HCID 71621784, compound

HRID 871014Notes

Reaction equation

HRID 871014 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC[CH2:11][NH:12][C:13]([NH:15][C:16]1[S:20][N:19]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C:17]=1[C:30]([NH2:32])=[O:31])=[O:14]>N1C=CC=CC=1>[C:5]([O:4][CH2:1][CH2:2][CH2:11][NH:12][C:13]([NH:15][C:16]1[S:20][N:19]=[C:18]([C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[C:17]=1[C:30]([NH2:32])=[O:31])=[O:14])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 71621783HCID 71621783, compound

Product 1

HCID 71621784HCID 71621784, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (4.2 g 0.041 mol) was added to a solution of 5-({[(3-hydroxypropyl)amino]carbonyl}amino)-3-(4-nitrophenyl)isothiazole-4-carboxamide (12.0 g, 0.032 mol) in pyridine (120 mL) at ambient temperature over 10 min. The resulting mixture was stirred at ambient temperature for 2 hr. The reaction mixture was concentrated in vacuo. The residue taken in EtOAc (500 mL) and washed with water and brine then dried (sodium sulfate), filtered, solvent concentrated in vacuo to give the title compound as a yellow solid (12.2 g, 92%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with water and brine
  3. dry with materialthen dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationsolvent concentrated in vacuo

Sources & evidence

ORD record
ord-3022fed86c984a1c9e24b4f0d0b45971
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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