Acetic Anhydride → HCID 22097136, compound

HRID 861528Notes

Reaction equation

HRID 861528 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:18])[N:9]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>CN(C1C=CN=CC=1)C.C(O)(=O)C.O1CCCC1>[C:20]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:18])[N:9]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 22097155HCID 22097155, compound

Product 1

HCID 22097136HCID 22097136, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

52.95 g (0.2 mol) of 7-amino-1-(ethoxycarbonylmethyl)-2,3(1H,4H)-quinoxalinedione and a spatula tip of 4-(N,N-dimethylamino)pyridine were suspended in a mixture of 500 ml of glacial acetic acid and 300 ml of tetrahydrofuran and heated to 50° C. Then 20.5 g (0.2 mol) of acetic anhydride were added dropwise and the mixture was heated at 50° C. for 2 h. The precipitate was filtered off with suction to yield 57.8 g (94%) of the product.

Workup

  1. temperaturethe mixture was heated at 50° C. for 2 h
  2. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-ae128d827df94cb4a30519ec3164e18b
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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