Acetic Anhydride → HCID 178504702, compound

HRID 1958443Notes

Reaction equation

HRID 1958443 reaction equation
[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[N:4][O:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:20](OC(=O)C)(=O)C>C(OCC)(OCC)OCC>[CH3:19][S:16]([C:13]1[CH:12]=[CH:11][C:10]([C:3]2[C:2]3[N:1]=[CH:20][N:9]=[C:7]([OH:8])[C:6]=3[O:5][N:4]=2)=[CH:15][CH:14]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 574963794-Amino-3-[4-(methanesulfonyl)phenyl]-1,2-oxazole-5-carboxamide

Product 1

HCID 178504702HCID 178504702, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

To a suspension of 4-amino-3-(4-methanesulfonyl-phenyl)-isoxazole-5-carboxylic acid amide (2.5 g, 8.9 mmol) in CH(OEt)3 (30 mL), was added acetic anhydride (10 mL) at ambient temperature. The reaction was heated to reflux for 5 h and cooled to room temperature. The reaction was concentrated under vacuum and poured into H2O (50 mL). The organic material was extracted with ethyl acetate (50 mL), dried over MgSO4 and concentrated under vacuum. The crude product was used for the next step without further purification. LCMS 292.0 [M+H].

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. concentrationThe reaction was concentrated under vacuum
  4. additionpoured into H2O (50 mL)
  5. extractionThe organic material was extracted with ethyl acetate (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-29b4a0050fe241adaa40e54a6c277b19
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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