Thionyl Chloride → HCID 14878529, compound

HRID 1381709Notes

Reaction equation

HRID 1381709 reaction equation
[C:1]1([CH2:7]/[C:8](=[N:16]/[NH:17]C(OC)=O)/[S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:22](Cl)(Cl)=O>ClCCl>[C:1]1([C:7]2[S:22][N:17]=[N:16][C:8]=2[S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14405974HCID 14405974, compound

Product 1

HCID 14878529HCID 14878529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (Z)-[2-phenyl-1-(phenylthio)ethylidene]hydrazinecarboxylic acid, methyl ester in 450 ml of dry dichloromethane was treated with 29.7 g of thionyl chloride. This mixture ws refluxed for one hour, then poured into chipped ice and extracted three times with ether. The extracts were combined, washed with 0.1N sodium hydroxide twice, water and saturated sodium chloride and dried. This material was evaporated onto 100 g of silica gel which was then poured onto a column of silica gel packed in petroleum ether. The column was eluted with a gradient of 20-60% dichloromethane in petroleum ether, giving 35 g of the desired compound as an orange oil. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 7.28 (bs, 5H, C6H5); 7.30-7.65 (m, 5H, C6H5). Infrared absorption spectrum (neat): 1580(m); 1475(s); 1440(s); 1286(w); 1265(m); 1255(m); 1240(w); 1025(w); 1005(w); 985(w); 935(m); 915(m); 805(m); 765(m); 745(s); 695(s).

Workup

  1. temperatureThis mixture ws refluxed for one hour
  2. additionpoured into chipped ice
  3. extractionextracted three times with ether
  4. washwashed with 0.1N sodium hydroxide twice
  5. dry with materialwater and saturated sodium chloride and dried
  6. customThis material was evaporated onto 100 g of silica gel which
  7. additionwas then poured onto a column of silica gel
  8. washThe column was eluted with a gradient of 20-60% dichloromethane in petroleum ether

Sources & evidence

ORD record
ord-7cf5b39ef1bb4cfab90c45162c8727fa
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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