Sulfuric Acid → HCID 54028995, compound
Reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:18](#[N:20])[CH3:19]>>[CH3:6][CH:7]([NH:20][C:18](=[O:2])[CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]Participants
Procedure
To 80 g (0.8 mole) 97% sulfuric acid was slowly added over a period of 1/2 hour with stirring, a mixture of 12 g acetonitrile and 34 g 1-dodecene, the temperature being maintained at 25°-30° C. with an ice-bath. The reaction mixture was stirred and cooled for an additional 2 hours, until no more heat evolved. The reaction mixture was stirred at room temperature for an additional 21/2 hours and then poured into 200 ml ice water and allowed to separate in a separatory funnel. The top layer was again poured into 200 ml ice water, neutralized with about 45 g sodium carbonate, extracted with ether, dried over Na2SO4 and evaporated in vacuum to 39.6 g of a yellow oil. Kugelrohr distillation gave 34 g of N-β-dodecylacetamide boiling at 120°-160° C. (50μ) and having a m.p. of 41°-49° C. Analysis of the end product showed that less than 2% of the product had hydrolyzed to amine.
Workup
- temperaturethe temperature being maintained at 25°-30° C. with an ice-bath
- stirringThe reaction mixture was stirred
- temperaturecooled for an additional 2 hours
- temperatureuntil no more heat
- stirringThe reaction mixture was stirred at room temperature for an additional 21/2 hours
- customto separate in a separatory funnel
- additionThe top layer was again poured into 200 ml ice water
- extractionextracted with ether
- dry with materialdried over Na2SO4
- customevaporated in vacuum to 39.6 g of a yellow oil
- distillationKugelrohr distillation
Sources & evidence
- ORD record
- ord-5ceebd0215aa436a80658ae268c9ba3a
- Source dataset
- uspto-grants-1981_08
- Patent number
- US04283192
Reaction notes
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