Methyl propiolate → HCID 17878067, compound

HRID 249612Notes

Reaction equation

HRID 249612 reaction equation
[C:1]([N:20]=[N+:21]=[N-:22])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][CH3:28])(=[O:26])[C:24]#[CH:25]>CC(C)=O.CCOCC>[CH3:28][O:27][C:23]([C:24]1[N:22]=[N:21][N:20]([C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:25]=1)=[O:26]

Participants

5

Reactant 2

HCID 13536Methyl propiolateHCID 84340Benzene, 1,1',1''-(azidomethylidyne)tris-

Product 1

HCID 17878067HCID 17878067, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of sodium azide (19.0 g : 0.283 Mol.) in dimethyl- formamide (130 ml) is added trityl chloride (76.0 g : 0.273 Mol.), and the mixture is stirred at room temperature for 5 hours. The reaction mixture is diluted with water and extracted with ether. The extract is washed with brine, dried over sodium sulfate, and concentrated to give trityl azide. To a solution of this azide in acetone (300 ml) is added methyl propiolate (24 ml : 0.27 Mol.), and the mixture is heated under reflux for 6 days. The reaction mixture is cooled to the room temperature and diluted with ether. The separating crystals are collected by filtration to give 1-trityl-1,2,3-triazol-4-ylcarboxylic acid methyl ester (62.0 g) as colorless crystals. Yield: 62%. mp. 189° to 190° C. NMR δ (CDCl3) ppm: 3.93(s, 3H), 7.05-7.15(m, 6H), 7.3-7.4(m, 9H), 8.02(s, 1H).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 days
  3. filtrationThe separating crystals are collected by filtration

Sources & evidence

ORD record
ord-fae735354a4a412b923647abaab0c635
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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