Dichloromethane → HCID 14441136, compound

HRID 892722Notes

Reaction equation

HRID 892722 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][NH:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19])=[O:13].C(Cl)Cl>CN(C=O)C>[O:19]=[C:15]1[CH2:16][CH2:17][CH2:18][N:14]1[C:12](=[O:13])[NH:11][CH2:10][CH2:9][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 14441091HCID 14441091, compound

Product 1

HCID 14441136HCID 14441136, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 1.9 g (27.5 mmol) of 1,2,4-triazole in 15 ml of DMF was added 1.1 g (27.5 mmol) of 60% NaH, and the mixture was heated at 90° C. for about 2 hr. Then, 13 ml of DMF containing 3.50 g (18.4 mmol) of 1-[(2-chloroethyl)carbamoyl]-2-oxopyrrolidine (III-1) was added to the mixture, which was heated at 90° C. for 4.5 hr. The reaction solution was poured into CH2Cl2, and the insoluble material was removed by filtration. After evaporating the solvent, the CH2Cl2 layer was refined by silica gel column chromatography, whereby 2.28 g (55.6%) of the objective compound (Ia-34) was obtained from the eluate with CH2Cl2 -methanol (20/1 v/v). The crystals melting at 106.0°-107.0° C. were obtained by recrystallizing from ethanol.

Workup

  1. temperaturewas heated at 90° C. for 4.5 hr
  2. customthe insoluble material was removed by filtration
  3. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-20a0a1148def45c5975dd425ff2496b5
Source dataset
uspto-grants-1992_06
Patent number
US05120733

Reaction notes

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