Acetic Anhydride → HCID 67785256, compound

HRID 1770209Notes

Reaction equation

HRID 1770209 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([CH:11]1[CH2:15][S:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][CH2:24][O:25][N+:26]([O-:28])=[O:27])[NH:12]1)([OH:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[C:1]([N:12]1[CH:11]([C:8]([OH:10])=[O:9])[CH2:15][S:14][CH:13]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][CH2:24][O:25][N+:26]([O-:28])=[O:27])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic Anhydride3×HCID 11430Potassium Carbonate3×HCID 20095533HCID 20095533, compound

Product 1

HCID 67785256HCID 67785256, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.9 ml of acetic anhydride in THF was added slowly at 0° C. to a solution of 2 g of the compound from Example XVI and 2.1 g of potassium carbonate in H2O. The resulting solution was stirred for 1 hour, after which 1.0 g of potassium carbonate was added to the reaction mixture, followed by the addition of 1 ml of acetic anhydride. The reaction mixture was stirred for one and a half hours, after which a further 1.0 g of potassium carbonate and 1 ml of acetic anhydride were added. After finally stirring for a further 30 minutes, the solution was concentrated under vacuum and cooled in ice. The addition of dilute sulphuric acid gave a precipitate. This precipitate was filtered off, dried and recrystallised from methanol/ether. Yield 60%. Empirical formula C14H16N2O7S. Molecular weight 356. Melting point 159°-162° C. TLC system: ethyl acetate:methanol/1:1. Rf 0.50.

Workup

  1. stirringThe reaction mixture was stirred for one and a half hours
  2. stirringAfter finally stirring for a further 30 minutes
  3. concentrationthe solution was concentrated under vacuum
  4. temperaturecooled in ice
  5. additionThe addition of dilute sulphuric acid
  6. customgave a precipitate
  7. filtrationThis precipitate was filtered off
  8. customdried
  9. customrecrystallised from methanol/ether

Sources & evidence

ORD record
ord-7589b529f05b42f6a42f0f656102db27
Source dataset
uspto-grants-1995_01
Patent number
US05385922

Reaction notes

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