Diisopropyl Ether → HCID 14294115, compound

HRID 1381694Notes

Reaction equation

HRID 1381694 reaction equation
[S:1]=[C:2](C(S)C(OCC)=O)[CH3:3].[NH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH2:12].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2].C(OC(C)C)(C)C>ClCCl>[S:1]=[C:2]([NH:12][NH:11][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:3]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 66225Magnesium orthosilicateHCID 86742729HCID 86742729, compound

Product 1

HCID 14294115HCID 14294115, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 110 g of 2-(1-thioxoethyl)thioglycolic acid, ethyl ester, 65.2 g of ethyl hydrazinocarboxylate and 500 ml of dichloromethane was heated at reflux for 3 hours, then concentrated in vacuo. The oily residue was concentrated further under high vacuum, giving a yellow oil. This oil was dissolved in 500 ml of dichloromethane and passed through a bed of hydrous magnesium silicate, washing with additional dichloromethane. The resulting light yellow oil was crystallized from diisopropyl ether giving a 79% yield of the desired compound as ivory crystals, mp 54.0°-57.5° C. Proton nuclear magnetic resonance (δ [ppm], CDCl3) 90 MHz: 1.30 (t, 3 H, J=7.4 Hz, CH3CH2); 2.55 (s, 3H, CH3CS); 4.25 (q, 2H, CH2CH3); 8.75 (bs, 1H, NH); 10.35 (bs, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. concentrationThe oily residue was concentrated further under high vacuum
  5. customgiving a yellow oil
  6. washwashing with additional dichloromethane

Sources & evidence

ORD record
ord-85f0c3be7b0c4ae0a7116e4927a1dd08
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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