Isopropanol → Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate

HRID 841970Notes

Reaction equation

HRID 841970 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.[OH2:26].[C:27]1([CH3:37])[CH:32]=CC(S(O)(=O)=O)=C[CH:28]=1.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39].[CH:50]([OH:53])([CH3:52])[CH3:51]>C(Cl)Cl>[CH:50]([O:53][C:38]([O:39][CH:32]([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)[CH:27]([CH3:28])[CH3:37])=[O:26])([CH3:52])[CH3:51]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 682631,1'-CarbonyldiimidazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 178470514HCID 178470514, compound

Product 1

HCID 22222564Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylateYield 367%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (Synthesis Example 2) (1.07 g) and p-toluenesulfonic acid monohydrate (53 mg) were suspended in methylene chloride (10 ml) under an argon atmosphere. Isobutyl aldehyde (330 mg) was added to the suspension. The mixture was stirred at room temperature for 25 min. 1,1′-carbonyldiimidazole (744 mg) and methylene chloride (5.0 ml) were added thereto, and the mixture was stirred at room temperature for 25 min. Isopropyl alcohol (920 mg) was added thereto, and the mixture was stirred at room temperature for 3 hr and then refluxed for 21 hr. The mixture was post-treated by a conventional method and subjected to separation and purification to give ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5 (4,5-dimethoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate as a light yellow foam (520 mg, 34%).

Workup

  1. stirringthe mixture was stirred at room temperature for 25 min
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. temperaturerefluxed for 21 hr
  4. additionThe mixture was post-treated by a conventional method
  5. customsubjected to separation and purification

Sources & evidence

ORD record
ord-2a9149dabc094a7d9ee46212cf7bded1
Source dataset
uspto-grants-2002_04
Patent number
US06372735B1

Reaction notes

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