Sodium Iodide → HCID 14441149, compound

HRID 1590195Notes

Reaction equation

HRID 1590195 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])=[O:6].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH2:2][CH2:3][NH:4][C:5]([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])=[O:6])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 14441091HCID 14441091, compound

Product 1

HCID 14441149HCID 14441149, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2.10 g (11.0 mmol) of 1-[2-chloroethylcarbamoyl]-2-oxopyrrolidine and 1.40 g (10 mmol) of 4-methoxybenzenethiol in 25 ml of DMF were added 2.47 g (16.5 mmol) of NaI and 3.02 g (22 mmol) of K2CO3, and the mixture was heated at 100° C. for 4.5 hr. The reaction solution was poured into ethyl acetate, washed with water, diluted hydrochloric acid, water, and saturated brine in order. After drying, the solvent was removed by evaporation. The residue was refined by silica gel column chromatography, whereby 2.78 g (94.6%) of the crystalline objective compound (Ia-45) was obtained from the eluate with benzene/ethyl acetate (8/1-5/1 v/v). The needles melting at 64.0°-65.0° C. are obtained by recrystallizing from ether - n-hexane. The properties of the objective compound (Ia-45) are shown in Table 7.

Workup

  1. washwashed with water, diluted hydrochloric acid, water, and saturated brine in order
  2. customAfter drying
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-fc631844c01648448994a93cff242b10
Source dataset
uspto-grants-1993_04
Patent number
US05202345

Reaction notes

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