Acetonitrile → HCID 70485151, compound

HRID 1248282Notes

Reaction equation

HRID 1248282 reaction equation
O.Cl.Cl.[NH:4]1[CH2:8][CH2:7][N:6]=[C:5]1[CH:9]([O:11][C:12]1[C:13]([CH3:19])=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1)[CH3:10].C(#N)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[OH2:11].[NH:6]1[CH2:7][CH2:8][N:4]=[C:5]1[CH:9]([O:11][C:12]1[C:13]([CH3:19])=[C:14]([NH:18][C:23](=[O:25])[CH3:24])[CH:15]=[CH:16][CH:17]=1)[CH3:10].[NH:6]1[CH2:7][CH2:8][N:4]=[C:5]1[CH:9]([O:11][C:12]1[C:13]([CH3:19])=[C:14]([NH:18][C:23](=[O:25])[CH3:24])[CH:15]=[CH:16][CH:17]=1)[CH3:10]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 20279317HCID 20279317, compound

Product 1

HCID 70485151HCID 70485151, compound

Procedure

The title compound of Example 4 (1.5 g, 4.8 mmole) was stirred in 60 ml of acetonitrile containing 2.3 ml (ca. 24 mmole) of acetic anhydride. After 18 hours the reaction mixture was concentrated to dryness in vacuo and the residue was dissolved in water. The solution was then made alkaline with aqueous sodium bicarbonate and extracted with dichloromethane. After the organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo, the residue was recrystallized from diethyl ether to give 398 mg of the title compound. Structure assignment was supported by nmr spectrum and by elemental analysis.

Workup

  1. concentrationAfter 18 hours the reaction mixture was concentrated to dryness in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. dry with materialAfter the organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-6316b7fd279f4857b1d530903f5b88b9
Source dataset
uspto-grants-1985_06
Patent number
US04523020

Reaction notes

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