Chloroacetonitrile → HCID 14371873, compound

HRID 1381954Notes

Reaction equation

HRID 1381954 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2([C:15](=[O:16])[N:14]([OH:17])[C:13](=[O:18])[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:24][C:25]#[N:26].C(OCC)(=O)C>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2([C:15](=[O:16])[N:14]([O:17][CH2:24][C:25]#[N:26])[C:13](=[O:18])[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14371872HCID 14371872, compound

Product 1

HCID 14371873HCID 14371873, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-tert-butyloxycarbonyl-2-hydroxy-2,8-diazaspiro[4,5]decane-1,3-dione (0.56 g) in dimethylformamide (5 ml) was added 88 mg of sodium hydride (60% in oil), and the mixture was stirred for one hour at room temperature. To the mixture was added chloroacetonitrile (140 μl). The whole mixture was stirred for 2 hours at room temperature, to which was added ethyl acetate (30 ml), followed by washing with a saturated aqueous solution of sodium hydrogencarbonate and then with a 10% aqueous solution of citric acid. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated off. The residue was recrystallized from ethyl acetate-diethyl ether to obtain 0.53 g of a colorless solid, m.p. 138° to 139° C.

Workup

  1. stirringThe whole mixture was stirred for 2 hours at room temperature, to which
  2. washby washing with a saturated aqueous solution of sodium hydrogencarbonate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated off
  5. customThe residue was recrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-547595b51f624b7193ab7c1d854c6e3b
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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