Thionyl Chloride → HCID 12798028, compound

HRID 1106024Notes

Reaction equation

HRID 1106024 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11](O)=[O:12])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].S(Cl)([Cl:19])=O>>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([Cl:19])=[O:12])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12798027HCID 12798027, compound

Product 1

HCID 12798028HCID 12798028, compound

Procedure

2-(4-Azidophenyl)-3-methylbutanoic acid, 3.68 g, was dissolved in 15 ml of thionyl chloride. After 45 minutes the solution was heated to a boil, then evaporated in vacuum to a residual oil. The oil was twice dissolved in diethyl ether and evaporated in vacuum to a residual oil, and further dried under a nitrogen stream. The infrared spectrum of the oil showed absorption peaks at 2120 cm-1 (azide) and 1810 cm-1 (acid chloride).

Workup

  1. temperatureAfter 45 minutes the solution was heated to a boil
  2. customevaporated in vacuum to a residual oil
  3. dissolutionThe oil was twice dissolved in diethyl ether
  4. customevaporated in vacuum to a residual oil
  5. customfurther dried under a nitrogen stream
  6. customabsorption peaks at 2120 cm-1 (azide) and 1810 cm-1 (acid chloride)

Sources & evidence

ORD record
ord-91549dc9d53146e1af864129512a8078
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

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