Propargyl alcohol → HCID 135737573, compound

HRID 1448192Notes

Reaction equation

HRID 1448192 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[N+:12]=[N-:13])[C:5](=[O:11])[NH:6]2.[CH2:14]([OH:17])[C:15]#[CH:16]>CCOCC>[Cl:1][C:2]1[C:3]2[C:4]3[N:12]([N:13]=[C:15]([CH2:14][OH:17])[CH:16]=3)[C:5](=[O:11])[NH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 178514321HCID 178514321, compound

Product 1

HCID 135737573HCID 135737573, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 g (0.0103 mole) of 4-chloro-3-diazooxindole, and 11.95 g (0.207 mole or 20 equivalents) of 97% propargyl alcohol are refluxed under N2 for hours. The reaction mixture is cooled, diluted with ether (200 ml) and stirred for 20 minutes. The cream-colored precipitates are filtered off, washed with ether and dried in vacuo over the weekend at 50°. Yield: 2.44 g, mp 295°-296°; 94.9% crude yield. The crude product is taken up in absolute ethanol, filtered while hot and the filtrate is concentrated to a volume of 150 ml. The solution is cooled and the precipitates filtered off, washed with ether and dried in vacuo at room temperature for 24 hours to give 1.4 g of title compound, mp 309°-311°.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe cream-colored precipitates
  3. filtrationare filtered off
  4. washwashed with ether
  5. customdried in vacuo over the weekend at 50°
  6. filtrationfiltered while hot and the filtrate
  7. concentrationis concentrated to a volume of 150 ml
  8. temperatureThe solution is cooled
  9. filtrationthe precipitates filtered off
  10. washwashed with ether
  11. customdried in vacuo at room temperature for 24 hours

Sources & evidence

ORD record
ord-3f53d3fd4aa84088a10c5859cb9eae71
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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