Ethyl Acetate → HCID 24697918, compound

HRID 1917074Notes

Reaction equation

HRID 1917074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.Cl.Cl[CH2:12][CH2:13][NH2:14].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CC#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:12][CH2:13][NH2:14])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 849893-MethoxybenzenethiolHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 24697918HCID 24697918, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-methoxybenzenethiol (5 g), 2-chloroethylamine hydrochloride (1.1 eq.) and Cs2CO3 (2.2 eq.) in CH3CN (60 mL) was stirred at 60° C. for 20 h. To the reaction mixture, EtOAc (100 mL) was added, and washed with H2O (2×30 mL). The organic phase was concentrated under reduced pressure to give product 20 (Yield: 6.2 g, 95%), which appeared to be pure by TLC and NMR and was used for the next step reaction without further purification.

Workup

  1. washwashed with H2O (2×30 mL)
  2. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-047c30e6965b473b808f5416d33296cc
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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