Sulfuric Acid → A 643C

HRID 1277491Notes

Reaction equation

HRID 1277491 reaction equation
S(=O)(=O)(O)O.[NH2:6][CH2:7][C:8]#[N:9].[CH3:10][C:11](O)([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:12].S(=O)(=O)(O)[OH:20]>C(O)(=O)C>[NH2:9][CH2:8][C:7]([NH:6][C:11]([CH3:12])([CH3:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:20]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 122422-Methyl-2-heptanolHCID 196971Aminoacetonitrile sulfate (1:1)

Product 1

HCID 128299A 643C

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of aminoacetonitrile bisulphate (15.4 g, 0.1 mol) and 2-methylheptan-2-ol (13.0 g, 0.1 mol) in acetic acid (60 ml) was treated with concentrated sulphuric acid (12 ml) with the temperature held at 40°-45° C. After stirring for 1 hour the mixture was poured into ice-water (300 ml) and washed with ether (2×200 ml). The aqueous phase was basified with 10 N sodium hydroxide solution, extracted with ether (3×200 ml) and the combined extracts were dried over magnesium sulphate then distilled to give 2-amino-N-(1,1-dimethylhexyl)acetamide as a colourless oil, b.p. 104°-110° C. at 0.2 mm Hg.

Workup

  1. customheld at 40°-45° C
  2. washwashed with ether (2×200 ml)
  3. extractionextracted with ether (3×200 ml)
  4. dry with materialthe combined extracts were dried over magnesium sulphate
  5. distillationthen distilled

Sources & evidence

ORD record
ord-cc55343d309446d5b8080acbaab4b0b6
Source dataset
uspto-grants-1981_07
Patent number
US04277498

Reaction notes

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