Sodium Azide → A 643C

HRID 1277488Notes

Reaction equation

HRID 1277488 reaction equation
[N-:1]=[N+]=[N-].[Na+].Cl[CH2:6][C:7]([NH:9][C:10]([CH3:17])([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:8]>O.CO.[Pd]>[NH2:1][CH2:6][C:7]([NH:9][C:10]([CH3:17])([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:8]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 234541292-chloro-N-(1,1-dimethylhexyl)acetamide

Product 1

HCID 128299A 643C

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium azide (6.7 g, 103 m mol) in water (56 ml) and methanol(104 ml) was treated with 2-chloro-N-(1,1-dimethylhexyl)acetamide (16.5 g, 80 m mol) and the mixture was refluxed for 5 hours. After cooling, the mixture was extracted with 40-60 petrol (3×200 ml), the extracts were dried over magnesium sulphate and evaporated under reduced pressure to give crude 2-azido-N-(1,1-dimethylhexyl)acetamide as a pale yellow oil.This oil was dissolved in methanol (200 ml) and hydrogenated over 10% palladium on charcoal (3.2 g) at atmospheric pressure and room temperaturefor 24 hours. The mixture was filtered and the filtrate evaporated to give a crude oil (13.6 g) which was distilled to give 2-amino-N-(1,1-dimethylhexyl)acetamide as a colourless oil, b.p. 88°-90° C. at 0.05 mm Hg.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with 40-60 petrol (3×200 ml)
  4. dry with materialthe extracts were dried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customto give crude 2-azido-N-(1,1-dimethylhexyl)acetamide as a pale yellow oil.This oil
  7. filtrationThe mixture was filtered
  8. customthe filtrate evaporated
  9. customto give a crude oil (13.6 g) which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-cddad38ba6704f9f9ec0919f9cdb3989
Source dataset
uspto-grants-1981_07
Patent number
US04277498

Reaction notes

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