2-Pyrrolidone → N-(m-Trifluoromethylphenyl)-3-methylthio-4-chloromethyl-2pyrrolidone

HRID 1390278

Reaction equation

HRID 1390278 reaction equation
[CH3:1][S-:2].[Na+].C[O-].[Na+].[F:7][C:8]([F:25])([F:24])[C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH:18]([CH2:20][Cl:21])[CH:17](Cl)[C:16]2=[O:23])[CH:12]=[CH:13][CH:14]=1.N1CCCC1=O>CN(C)C=O.CO>[F:7][C:8]([F:25])([F:24])[C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH:18]([CH2:20][Cl:21])[CH:17]([S:2][CH3:1])[C:16]2=[O:23])[CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 120252-PyrrolidoneHCID 91677FlurochloridoneHCID 4378561Sodium methanethiolateHCID 10942334Sodium Methoxide

Product 1

HCID 22748887N-(m-Trifluoromethylphenyl)-3-methylthio-4-chloromethyl-2pyrrolidoneYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In the same manner as descried above for Example 1, sodium methyl mercaptide prepared from 6.5 g of a 25% methanol solution of sodium methoxide in 50 ml of dimethylformamide was added to 9.4 g (0.034 mole) of N-(m-trifluoromethylphenyl)-3-chloro-4-chloromethyl-2-pyrrolidone (prepared according to the procedure described in U.S. Pat. No. 4,069,038). The product weighed 9.3 g, representing 85% yield based on the pyrrolidone, structure confirmed by NMR analysis, with refractive index nD30 =1.5028. This compound is shown in Table I as Compound No. 2.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-163e4b15a7334f219965573c1058670e
Source dataset
uspto-grants-1979_02
Patent number
US04138495

Linked notes

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