Ethyl propiolate → HCID 57426482, compound

HRID 1763460Notes

Reaction equation

HRID 1763460 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[N+:12]=[N-:13])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[C:15]#[CH:16]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:12]([N:13]=[C:15]([C:14]([O:18][CH2:19][CH3:20])=[O:17])[CH:16]=3)[C:7](=[O:11])[N:8](/[CH:16]=[CH:15]\[C:14]([O:18][CH2:19][CH3:20])=[O:17])[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 178514326HCID 178514326, compound

Product 1

HCID 57426482HCID 57426482, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7.5 g (0.039 mole) of 6-chloro-3-diazooxindole is suspended in 400 ml of xylene and 8.4 g (0.086 mole) of ethyl propiolate added. The reaction mixture is heated 7 hours in a 160° silicone oil bath under nitrogen. A brown solid forms on cooling to room temperature (9.0 g, 59% yield). Recrystallization from dichloromethanemethanol gives 8.5 g of analytically pure title compound, m.p. 215°-217°.

Workup

  1. temperatureThe reaction mixture is heated 7 hours in a 160° silicone oil bath under nitrogen
  2. customRecrystallization from dichloromethanemethanol

Sources & evidence

ORD record
ord-f1ffef6108044c80b335ea1e1209ea7a
Source dataset
uspto-grants-1978_09
Patent number
US04112098

Reaction notes

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