Ethyl 4-methylpent-2-ynoate → 1H-1,2,3-Triazole-5-carboxylic acid, 1-(2,6-dichlorophenyl)-4-(1-methylethyl)-, ethyl ester

HRID 424775Notes

Reaction equation

HRID 424775 reaction equation
[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3].[CH2:12]([O:14][C:15](=[O:21])[C:16]#[C:17][CH:18]([CH3:20])[CH3:19])[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15]([C:16]1[N:1]([C:4]2[C:5]([Cl:11])=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:10])[N:2]=[N:3][C:17]=1[CH:18]([CH3:20])[CH3:19])=[O:21])[CH3:13]

Participants

4

Reactant 2

HCID 11400823Ethyl 4-methylpent-2-ynoateHCID 116008082-Azido-1,3-dichloro-benzene

Product 1

HCID 667040591H-1,2,3-Triazole-5-carboxylic acid, 1-(2,6-dichlorophenyl)-4-(1-methylethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-azido-1,3-dichloro-benzene (1.0 g) and 4-methyl-pent-2-ynoic acid ethyl ester (1.8 g) in toluene (5 mL) is heated to 120° C. overnight. Two regioisomers are observed in a range of 1:1 to 3:1 in favor of the desired product. The reaction is concentrated under reduced pressure and the residue is purified by flash chromatography, eluting with 5% ethyl acetate in hexanes. 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 2H), 7.42 (t, 1H), 4.22 (q, 2H), 3.64 (m, 1H), 1.46 (d, 6H), 1.15 (t, 3H).

Sources & evidence

ORD record
ord-02ddf2096b9c429dad37f7d8ed22fea6
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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