Sodium Hydroxide → HCID 14294117, compound

HRID 1381695Notes

Reaction equation

HRID 1381695 reaction equation
[C:1]1([CH2:7][C:8](C(S)C(O)=O)=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[NH:17]([C:19]([O:21][CH3:22])=[O:20])[NH2:18]>O>[C:1]1([CH2:7][C:8]([NH:18][NH:17][C:19]([O:21][CH3:22])=[O:20])=[S:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 80519Methyl carbazateHCID 54023316HCID 54023316, compound

Product 1

HCID 14294117HCID 14294117, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 86.0 g of 2-(2-phenyl-1-thioxoethyl)thioglycolic acid, 195 ml of 2N sodium hydroxide and 100 ml of water was added dropwise to a suspension of 50 g of methyl hydrazinocarboxylate in 200 ml of water with vigorous stirring. Stirring was continued overnight, then the mixture was extracted twice with ether. The extracts were combined, washed successively with 5% aqueous sodium bicarbonate (twice), water and saturated aqueous sodium chloride, dried and concentrated in vacuo. The dark orange oil was purified by percolation through a bed of hydrous magnesium silicate with dichloromethane. The resulting pale yellow oil was chromatographed on a 70×850 mm dry column of silica gel, eluting with dichloromethane. The resulting oil was crystallized from toluene-hexane, giving 42.6 g of the desired compound as yellow crystals, mp 93.5°-94° C. Proton nuclear magnetic resonance (δ[ppm], CDCl3) 90 MHz: 3.79 (s, 3H, OCH3); 4.11 (s, 2H, CH3CS); 7.33 (bs, 5H, C6H5); 8.65 (bs, 1H, NH); 9.55 (bs, 1H, NH).

Workup

  1. extractionthe mixture was extracted twice with ether
  2. washwashed successively with 5% aqueous sodium bicarbonate (twice), water and saturated aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe dark orange oil was purified by percolation through a bed of hydrous magnesium silicate with dichloromethane
  6. customThe resulting pale yellow oil was chromatographed on a 70×850 mm
  7. customdry column of silica gel
  8. washeluting with dichloromethane
  9. customThe resulting oil was crystallized from toluene-hexane

Sources & evidence

ORD record
ord-b49d2b24169f4043acf98bd3040428ae
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

Loading…