cis-1,2-Dichloroethylene → HCID 10922798, compound

HRID 1053510Notes

Reaction equation

HRID 1053510 reaction equation
Cl/[CH:2]=[CH:3]\Cl.[C:5]1([S-:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Na+]>CN(P(N(C)C)(N(C)C)=O)C>[C:5]1([S:11]/[CH:6]=[CH:5]\[S:11][C:3]2[CH:2]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 643833cis-1,2-DichloroethyleneHCID 4110039Sodium benzenethiolate

Product 1

HCID 10922798HCID 10922798, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of (Z)-1,2-dichloroethene (0.49 g, 5.04 mmol) and compound 43 (2.0 g, 15.15 mmol) in HMPA (10 mL) was stirred under nitrogen for 1 h. The solvent was removed under reduced pressure to give the crude product that was then purified by column chromatography using 100% hexane as a solvent to give control (1.04 g, 85%). 1H NMR (400 MHz, CDCl3) δ 6.55 (s, 2H), 7.29 (m, 2H), 7.35 (t, J=7.7 Hz, 4H), 7.43 (s, 2H), 7.44 (m, 2H). HRMS ESI (m/z): Calculated for C14H12S2 [M]+: 244.0380. found: 244.0377.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2298a1ccd349495cb44024a566acfca6
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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