2-Chloroethyl methyl sulfide → HCID 86619000, compound

HRID 253527Notes

Reaction equation

HRID 253527 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N:12]([CH3:14])[CH3:13])[C:3]=1[N:15]1[C:19]([NH:20][CH3:21])=[C:18]([S:22][C:23]([F:26])([F:25])[F:24])[C:17]([C:27]#[N:28])=[N:16]1.ClC[CH2:31][S:32][CH3:33].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:42]CCCCCC.C(OCC)(=O)C>C(#N)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[C:4]([N:12]([CH3:13])[CH3:14])[C:3]=1[N:15]1[C:19]([N:20]([CH3:42])[CH2:21][CH2:31][S:32][CH3:33])=[C:18]([S:22][C:23]([F:24])([F:25])[F:26])[C:17]([C:27]#[N:28])=[N:16]1

Participants

7

Reactant 4

HCID 109652-Chloroethyl methyl sulfideHCID 62657Potassium Phosphate, TribasicHCID 21899848Ethylacetate heptaneHCID 86619001HCID 86619001, compound

Product 1

HCID 86619000HCID 86619000, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-(2-chloro-6-dimethylamino-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylthiopyrazole (Compound number 4-01, 0.29 g, 0.7 mmol) in acetonitrile (6 ml) was added chloroethyl methylsulfide (87 mg, 0.8 mmol) and potassium phosphate (0.42 g, 2.0 mmol). The mixture was heated under reflux for 4 hours. After extractive workup (heptane-ethyl acetate, water) and reverse HPLC chromatography the title product was obtained (0.16 g), 1H-NMR: 1.99 (3H), 2.31 (2H), 2.69 (6H), 2.85 (3H), 3.18 (2H), 7.15 and 7.29; 19F-NMR: −44.7, −63.9.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours

Sources & evidence

ORD record
ord-57831c7df00842d8be7892b1b4017f97
Source dataset
uspto-grants-2011_01
Patent number
US07872038B2

Reaction notes

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