Acetic Anhydride → HCID 20823162, compound

HRID 585262Notes

Reaction equation

HRID 585262 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)=[O:11])[C:6]([OH:8])=O.[C:19](OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]([NH:9][C:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)=[O:11])[C:6](=[O:8])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20823125HCID 20823125, compound

Product 1

HCID 20823162HCID 20823162, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2-[(5-Methyl-thiophene-2-carbonyl)-amino]-succinic acid 4-methyl ester (12 g, 45 mmol), pyridine (60 mL) and acetic anhydride (50 mL) were combined in a 500 mL flask. The reaction mixture was heated at 90° C. for 2 h and then cooled to ambient temperature. After concentrating the reaction mixture under reduced pressure, DI water was added (100 mL). (Potential exotherm!). The reaction mixture was partitioned between water and CH2Cl2. The organic phase was washed with 1N HCl and then dried (MgSO4), filtered and concentrated under reduced pressure. The material was used without further purification. MS (EI) 270.1 (M+H).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationAfter concentrating the reaction mixture under reduced pressure, DI water
  3. additionwas added (100 mL)
  4. customThe reaction mixture was partitioned between water and CH2Cl2
  5. washThe organic phase was washed with 1N HCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe material was used without further purification

Sources & evidence

ORD record
ord-9e9c8a12231a4c21a45ba5e0b0231918
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

Loading…