Acetonitrile → HCID 178498940, compound

HRID 1447197Notes

Reaction equation

HRID 1447197 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:7][C:8]1([CH3:20])[CH2:13][CH:12]([CH3:14])[CH2:11][CH:10]([O:15][C:16](=S)[NH:17][NH2:18])[CH2:9]1.[C:21](#N)[CH3:22]>>[CH3:7][C:8]1([CH3:20])[CH2:13][CH:12]([CH3:14])[CH2:11][CH:10]([O:15][C:16]2[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:21]([CH3:22])[NH:18][N:17]=2)[CH2:9]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7295Methyl chloroacetateHCID 20551615HCID 20551615, compound

Product 1

HCID 178498940HCID 178498940, compound

Procedure

At room temperature and while stirring, 84 g of methyl 2-chloroacetate is added to a solution, in 250 ml of acetonitrile, of the thiocarbazic acid-O-(3,3,5-trimethylcyclohexyl)-ester obtained in this manner. After stirring for 12 hours at room temperature, the mixture of solids which has precipitated out is separated by filtration and washed with acetone. The solids mixture is then stirred into 200 ml of aqueous ammonia solution (12 wt%) and subsequently extracted twice with methylene chloride (150 ml each time). After the methylene chloride solution has been dried over sodium sulfate, the solvent is evaporated. The solid which remains has, after recrystallization from a 2:1 mixture of toluene and n-hexane, a melting point of 167° to 168° C. and has, according to combustion analysis and nmr spectroscopy, the composition: ##STR12##

Workup

  1. customobtained in this manner
  2. stirringAfter stirring for 12 hours at room temperature
  3. additionthe mixture of solids which
  4. customhas precipitated out
  5. customis separated by filtration
  6. washwashed with acetone
  7. stirringThe solids mixture is then stirred into 200 ml of aqueous ammonia solution (12 wt%)
  8. extractionsubsequently extracted twice with methylene chloride (150 ml each time)
  9. dry with materialAfter the methylene chloride solution has been dried over sodium sulfate
  10. customthe solvent is evaporated
  11. customafter recrystallization
  12. additionfrom a 2:1 mixture of toluene and n-hexane

Sources & evidence

ORD record
ord-eea267daf27546a19c19ddc01787e98b
Source dataset
uspto-grants-1982_02
Patent number
US04316040

Reaction notes

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