Sulfuric Acid → 2-chloro-N-(1,1-dimethylhexyl)acetamide
Reaction equation
[Cl:1][CH2:2][C:3]#[N:4].[CH3:5][C:6](O)([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:7].S(=O)(=O)(O)[OH:15]>C(O)(=O)C>[Cl:1][CH2:2][C:3]([NH:4][C:6]([CH3:7])([CH3:5])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
A solution of chloroacetonitrile (15.1 g., 0.2 mol) and 2-methylheptan-2-ol (26.0 g., 0.2 mol) in acetic acid (120 ml) was treatedwith concentrated sulphuric acid (24 ml) with the temperature maintained at40°-50° C. After stirring for 1/2 hour the mixture was pouredinto ice-water (500 ml) and extracted with ether (3×400 ml). The combined extracts were washed with aqueous sodium carbonate until neutral and then evaporated to give 2-chloro-N-(1,1-dimethylhexyl)acetamide as a colourless solid m.p. 36°-37° C., b.p. 60°-62°C. at 0.01 mm Hg.
Workup
- extractionextracted with ether (3×400 ml)
- washThe combined extracts were washed with aqueous sodium carbonate until neutral and
- customthen evaporated
Sources & evidence
- ORD record
- ord-50c2d3d6523c4b06a57a0a31f3db97b7
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04277498
Reaction notes
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