Triethylamine → HCID 66584193, compound

HRID 2074144Notes

Reaction equation

HRID 2074144 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][O:13][C:14]([C:16]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[NH:18][N:17]=1)=[O:15].C(N(CC)CC)C>ClCCl.CCOCC>[CH3:12][O:13][C:14]([C:16]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[N:18]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[N:17]=1)=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylate

Product 1

HCID 66584193HCID 66584193, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (5.20 mL, 35.08 mmol) was added to a cooled (0° C.) solution of 5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (5.400 g, 31.54 mmol) and triethylamine (7.40 mL, 53.08 mmol) in dichloromethane (60 mL), the reaction mixture was stirred at room temperature for 2 hours, then diluted with ether and washed with water and brine, dried over anhydrous MgSO4 and filtered. The organic solvent was removed in vacuo. The residue was purified column chromatography to give 5-nitropyrazole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (3.28 g, 34%). 1H NMR (300 MHz, CDCl3) δ 7.34 (s, 1H), 7.32-7.24 (m, 5H), 3.89 (s, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe organic solvent was removed in vacuo
  5. customThe residue was purified column chromatography

Sources & evidence

ORD record
ord-36747a37340c41c883104e7c3e3a1f58
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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