Dichloromethane → HCID 53890501, compound

HRID 27930Notes

Reaction equation

HRID 27930 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11]([CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[CH:20]=1.C([O-])([O-])=O.[K+].[K+].[C:27]([CH:29](Cl)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:31]=1)#[N:28]>CCOCC.CS(C)=O.C1COCC1>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11]([CH:13]([CH:17]([CH3:18])[CH3:19])[C:14]([O:16][CH:29]([C:27]#[N:28])[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([O:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:31]=3)=[O:15])=[CH:10][C:9]=2[CH:20]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 127745872-Chloro-2-(3-phenoxyphenyl)acetonitrileHCID 542046732-(5-Chloro-2-benzothienyl)-3-methylbutanoic acid

Product 1

HCID 53890501HCID 53890501, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10 ml methylene chloride, 10 ml THF, 2-(5-chloro-2-benzothienyl)-3-methylbutanoic acid (0.5 g), K2CO3 (0.25 g) and α-cyano-3-phenoxybenzyl chloride (0.42 g) is stirred at RT for 15 hours. Then 5 ml of DMSO is added and reaction mixture stirred for about 48 hours. The mixture is taken up in ether, washed with water and brine, dried over Na2SO4 and solvent removed. The crude product is plated developing with 10% ethyl acetate/hexane to give α-cyano-3-phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate.

Workup

  1. customreaction mixture
  2. stirringstirred for about 48 hours
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4 and solvent
  5. customremoved

Sources & evidence

ORD record
ord-cf38697a35bb42deafa3cb060ccaab2f
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

Loading…