Ethyl orthoformate → ethyl 2-(4-ethoxyheptan-4-yl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate

HRID 841972Notes

Reaction equation

HRID 841972 reaction equation
[CH3:1][O:2][C:3]1[C:20]([O:21][CH3:22])=[CH:19][C:6]([C:7]([C:9]2[NH:13][N:12]=[N:11][C:10]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:8])=[C:5]([N+:23]([O-:25])=[O:24])[CH:4]=1.O.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30](S(O)(=O)=O)=[CH:29][CH:28]=1.C(OCC)(OCC)[O:39][CH2:40][CH3:41]>C(Cl)Cl>[CH2:40]([O:39][C:31]([N:12]1[N:11]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([C:7](=[O:8])[C:6]2[CH:19]=[C:20]([O:21][CH3:22])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:23]([O-:25])=[O:24])=[N:13]1)([CH2:30][CH2:29][CH3:28])[CH2:32][CH2:27][CH3:37])[CH3:41]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 178470514HCID 178470514, compound

Product 1

HCID 22222635ethyl 2-(4-ethoxyheptan-4-yl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (Synthesis Example 2) (140 mg) and p-toluenesulfonic acid monohydrate (2 mg) were suspended in methylene chloride (2 ml) under an argon atmosphere. 4-Heptane (0.14 ml) and triethyl orthoformate (0.17 ml) were added to the suspension. The mixture was stirred at room temperature for 2 hr. Further, p-toluenesulfonic acid monohydrate (4.5 mg) was added thereto. The mixture was stirred at room temperature for 2 hr. The mixture was post-treated by a conventional method and subjected to separation and purification to give ethyl 2-(4-ethoxyheptan-4-yl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (160 mg, 82%) as a yellow powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hr
  2. additionThe mixture was post-treated by a conventional method
  3. customsubjected to separation and purification

Sources & evidence

ORD record
ord-f5b5075ca27e4646a812c0bf553b853e
Source dataset
uspto-grants-2002_04
Patent number
US06372735B1

Reaction notes

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