Acetic Anhydride → 7-Acetamido-1-cyclohexyl-2,3(1H,4H)-quinoxalinedione

HRID 1457559Notes

Reaction equation

HRID 1457559 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[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(O)(=O)C.CN(C1C=CN=CC=1)C>[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[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 22097212HCID 22097212, compound2×

Product 1

HCID 220971107-Acetamido-1-cyclohexyl-2,3(1H,4H)-quinoxalinedioneYield 98.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

18.3 g (70 mmol) of 7-amino-1-cyclohexylquinoxaline-2,3(1H,4H)-dione (product e2 from Example 2) were dissolved in 250 ml of acetic acid and, after a spatula tip of 4-(N,N-dimethylamino)pyridine had been added, 7.2 g (70 mmol) of acetic anhydride were added dropwise. The mixture was then stirred at room temperature for 30 min. The resulting precipitate was then filtered off with suction and dried to yield 20.8 g (98%) of the product. Melting point 227°-230° C. (decomposition).

Workup

  1. filtrationThe resulting precipitate was then filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-eb41e82d53c1489ea000edb42fcca6dd
Source dataset
uspto-grants-1998_12
Patent number
US05849743

Reaction notes

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