4-Methylbenzenethiol → HCID 420617, compound

HRID 1917076Notes

Reaction equation

HRID 1917076 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl.Cl[CH2:11][CH2:12][NH2:13].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CC#N.O>[C:2]1([CH3:1])[CH:7]=[CH:6][C:5]([S:8][CH2:11][CH2:12][NH2:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 78114-MethylbenzenethiolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 420617HCID 420617, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-methylbenzenethiol (1.24 g), 2-chloroethylamine HCl (2.3 g) and Cs2CO3 (5.3 g) in CH3CN (30 mL) was stirred at 50° C. for 2 days. To the reaction mixture were added EtOAc (50 mL) and H2O (30 mL). The organic phase was separated, washed with H2O (2×30 mL) and concentrated under reduced pressure to give product 24. Yield: 1.67 g, 95%.

Workup

  1. customThe organic phase was separated
  2. washwashed with H2O (2×30 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dedc7c25d024355aa26b20899173e4e
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

Loading…