Acetic Anhydride → HCID 178431810, compound

HRID 329213Notes

Reaction equation

HRID 329213 reaction equation
[CH:1]1([S:7][CH2:8][CH2:9][N:10]([N:16]=[O:17])[C@H:11]([C:13]([OH:15])=O)[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N(N[C@H](C(O)=O)C)=O.C(OC(=O)C)(=O)C>O>[CH:1]1([S:7][CH2:8][CH2:9][N+:10]2[N-:16][O:17][C:13](=[O:15])[C:11]=2[CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 53968955HCID 53968955, compoundHCID 55301213HCID 55301213, compound

Product 1

HCID 178431810HCID 178431810, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The oil obtained in Example 3, N-[2-cyclohexylthio)ethyl]-N-nitrosoalanine, is treated with 54 parts of acetic anhydride and allowed to stand for 4 days at room temperature. After that time, the reaction mixture is added to 500 parts of water and extracted with methylene chloride. The organic extracts are washed with water and aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and evaporated to dryness. The oil remaining is crystallized from ether by seeding and cooling. The crystalline material is recovered by filtration and dried to afford pure 3-[2-(cyclohexylthio)ethyl] -4-methylsydnone, melting at about 82°-83°. That compound is represented structurally by the following formula ##STR7##

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts are washed with water and aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe oil remaining is crystallized from ether
  6. temperaturecooling
  7. filtrationThe crystalline material is recovered by filtration
  8. customdried

Sources & evidence

ORD record
ord-f5049055581a4d2a9882c9d9720e3e32
Source dataset
uspto-grants-1977_04
Patent number
US04020079

Reaction notes

Loading…