Triethylamine → HCID 86589889, compound

HRID 2417550Notes

Reaction equation

HRID 2417550 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][CH2:7][C:8]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:9]=1)[CH3:2].[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.C(N(CC)CC)C.[Sn](Cl)(Cl)(Cl)Cl>ClCCl.C(O)C>[NH2:13][C:12]1[C:8]([CH2:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])[C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([Cl:24])=[CH:26][CH:27]=2)=[N:9][N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 24287Tin tetrachlorideHCID 22632516HCID 22632516, compound

Product 1

HCID 86589889HCID 86589889, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.5 g (4.7 mol) of ethyl[((1-benzyl-4-nitro-1H-pyrazol-3-yl)methyl)amino]acetate was dissolved in 50 ml of dichloromethane: 0.71 ml (5.6 mmol) of 4-chlorobenzoyl chloride and 0.85 ml (6.1 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 100 ml of ethanol. 5.3 g (23.5 mmol) of tin chloride was added to the obtained solution, and they were stirred at 70° C. overnight. The solvent was evaporated. Sodium carbonate and ethyl acetate were added to the residue, and they were vigorously stirred at room temperature. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. temperatureunder cooling with ice for 2 hours
  3. stirringwere stirred at 70° C. overnight
  4. customThe solvent was evaporated
  5. additionSodium carbonate and ethyl acetate were added to the residue, and they
  6. stirringwere vigorously stirred at room temperature
  7. customAfter the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product
  8. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-4b43f89a434744f1b715502af795cf2d
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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