Sulfuric Acid → A 643C

HRID 1277494Notes

Reaction equation

HRID 1277494 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH2:3].CC(=CCCCC)C.S(=O)(=O)(O)O.[NH2:22][CH2:23][C:24]#[N:25].S(=O)(=O)(O)[OH:27]>C(O)(=O)C>[NH2:25][CH2:24][C:23]([NH:22][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:27]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 123302-Methyl-2-hepteneHCID 275192-Methyl-1-hepteneHCID 196971Aminoacetonitrile sulfate (1:1)

Product 1

HCID 128299A 643C

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture (1:1.1) of 2-methylhept-1-ene and 2-methylhept-2-ene (4.0 g) was added to a suspension of aminoacetonitrile bisulphate (5.5 g; 1 mol equiv.) in acetic acid (22 ml). The resultant mixture was warmed to 40°. Conc. sulphuric acid (4.5 ml) was then added over 10 minutes with stirring, so that the temperature did not rise above 70°. The mixture was left for 1 hour and then poured into ice-water (200 g). The aqueous phase was washed with ether (2×100 ml), basified with 10 N sodium hydroxide solution (100 ml) (pH 14), and extracted with ether (3×100 ml). The combined ether extracts were washed with water (50 ml), dried, and evaporated in vacuo (Buchi; 20°) to give the product as a yellow oil, which was dried at 0.2 mm/0.5 h/r.t. By t.l.c., i.r. and n.m.r. this product was identical with 2-amino-N-(1,1-dimethylhexyl)acetamide prepared from 2-methylheptan-2-ol.

Workup

  1. customdid not rise above 70°
  2. washThe aqueous phase was washed with ether (2×100 ml)
  3. extractionextracted with ether (3×100 ml)
  4. washThe combined ether extracts were washed with water (50 ml)
  5. customdried
  6. customevaporated in vacuo (Buchi; 20°)

Sources & evidence

ORD record
ord-fec04d91e2dd465f9efff26f259459e7
Source dataset
uspto-grants-1981_07
Patent number
US04277498

Reaction notes

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