Isoamyl Nitrite → [[4-Chloro-2-[2-chloro-4-(methylsulfonyl)phenoxy]phenyl]thio]-acetic acid, ethyl ester

HRID 910845Notes

Reaction equation

HRID 910845 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(ON=O)CC(C)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20](N)=[C:19]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][C:26]=2[Cl:35])[CH:18]=1>C(#N)C.O>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:19]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][C:26]=2[Cl:35])[CH:18]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 12185Ethyl ThioglycolateHCID 692247814-Chloro-2-[2-chloro-4-(methylsulfonyl)phenoxy]-benzenamine

Product 1

HCID 86620104[[4-Chloro-2-[2-chloro-4-(methylsulfonyl)phenoxy]phenyl]thio]-acetic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl mercaptoacetate (0.11 ml) followed by isoamylnitrite (0.16 ml) were added to a solution of the product from example 15 step (i) (0.5 g) in dry acetonitrile (20 ml) and heated at 60° C. for 10 h. The mixture was diluted with water, extracted with diethylether, the organics dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with dichloromethane, yield 0.60 g.

Workup

  1. extractionextracted with diethylether
  2. customthe organics dried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography on silica eluting with dichloromethane, yield 0.60 g

Sources & evidence

ORD record
ord-128fd2c3e0804c67a2b19c2fe223d30c
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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