Propargyl alcohol → HCID 135737594, compound

HRID 1763510Notes

Reaction equation

HRID 1763510 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[C:4](=[N+:14]=[N-:15])[C:5](=[O:13])[NH:6]2.[CH2:16]([OH:19])[C:17]#[CH:18]>C(OCC)C.C(O)C>[Cl:1][C:2]1[C:3]2[C:4]3[N:14]([N:15]=[C:17]([CH2:16][OH:19])[CH:18]=3)[C:5](=[O:13])[NH:6][C:7]=2[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 178490626HCID 178490626, compound

Product 1

HCID 135737594HCID 135737594, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2.0 g (0.0089 mole) of the 4-chloro-7-methoxy-3-diazooxindole (prepared in part B) and 10.3 g of 97% propargyl alcohol are refluxed under argon for 4 hours and cooled. The reaction mixture is diluted with 200 ml of ethyl ether and stirred for ~20 minutes and cream-colored precipitates are filtered off. Yield: 2.53 g, m.p. 221°-222°; quantitative crude yield (theor.: 2.49 g). This crude product is taken up in 200 ml absolute ethanol, the clear solution filtered while hot and the filtrate concentrated down to a volume of 50 ml and cooled. The resulting precipitates are filtered off and dried in vacuo at 45° over the weekend to give 1.59 g of title compound, m.p. 230°-232°.

Workup

  1. temperaturecooled
  2. customcream-colored precipitates
  3. filtrationare filtered off
  4. customquantitative crude yield (theor.: 2.49 g)
  5. filtrationthe clear solution filtered while hot and the filtrate
  6. concentrationconcentrated down to a volume of 50 ml
  7. temperaturecooled
  8. customThe resulting precipitates
  9. filtrationare filtered off
  10. customdried in vacuo at 45° over the weekend

Sources & evidence

ORD record
ord-af5966475c554560b9fe65b686082bfc
Source dataset
uspto-grants-1978_09
Patent number
US04112096

Reaction notes

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