Nitromethane → HCID 21434885, compound

HRID 435929Notes

Reaction equation

HRID 435929 reaction equation
C(N(CC)C(=S)S[CH2:6][C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=1)C.[OH-:25].[K+].[N+:27]([CH3:30])([O-:29])=[O:28]>CO>[C:13]([C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[OH:17])[CH2:6][C:30]([CH2:6][C:7]1[CH:8]=[C:9]([C:18]([CH3:20])([CH3:19])[CH3:21])[C:10]([OH:25])=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH2:6][C:7]1[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]([OH:17])=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[N+:27]([O-:29])=[O:28])([CH3:14])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14797Potassium HydroxideHCID 1712545HCID 1712545, compound

Product 1

HCID 21434885HCID 21434885, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a rapidly stirred solution of 11.01 g of 3,5-di-t-butyl-4-hydroxybenzyl N,N-diethyldithiocarbamate in 100 ml of hot methanol was added a freshly prepared solution of 1.68 g of potassium hydroxide and 0.61 g of nitromethane. The resulting stirred mixture was refluxed under nitrogen for 24 hours. Upon cooling, 3.0 g of the product precipitated as white crystals, mp 199°-201° C. An additional 2.07 of pure product was obtained from the filtrate after recrystallization from acetonitrile and vacuum drying.

Workup

  1. temperaturewas refluxed under nitrogen for 24 hours
  2. temperatureUpon cooling
  3. custom3.0 g of the product precipitated as white crystals, mp 199°-201° C
  4. customAn additional 2.07 of pure product was obtained from the filtrate
  5. customafter recrystallization from acetonitrile and vacuum
  6. customdrying

Sources & evidence

ORD record
ord-471a794810274ed58d8bb282a87a978e
Source dataset
uspto-grants-1977_02
Patent number
US04007159

Reaction notes

Loading…