Triethyl orthoacetate → HCID 178499020, compound

HRID 329573Notes

Reaction equation

HRID 329573 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7]([NH:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[F:18])(=[O:9])=[O:8])[C:3]=1[C:19]([O:21][CH3:22])=[O:20].[C:23](OCC)(OCC)([O:25][CH2:26]C)[CH3:24]>C(O)(=O)C.C(#N)C>[F:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([F:17])[C:11]=1[NH:10][S:7]([C:4]1[C:3]([C:19]([O:21][CH3:22])=[O:20])=[C:2]([N:1]=[C:23]([O:25][CH3:26])[CH3:24])[NH:6][N:5]=1)(=[O:8])=[O:9]

Participants

5

Reactant 2

HCID 66221Triethyl orthoacetateHCID 178499018HCID 178499018, compound

Product 1

HCID 178499020HCID 178499020, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

5.0 g (15mmol) 5-amino-N-(2,6-difluorophenyl)-4-methoxycarbonylpyrazole-3-sulphonamide was heated under reflux with 50 ml acetonitrile, 2.1 ml (17.5 mmol) triethyl orthoacetate and 3 drops acetic acid for 8 hours. The undissolved residue was filtered and the filtrate concentrated. The residue was chromatographed with hexane/ethyl acetate over silica gel and recrystallised from ether.

Workup

  1. filtrationThe undissolved residue was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was chromatographed with hexane/ethyl acetate over silica gel
  4. customrecrystallised from ether

Sources & evidence

ORD record
ord-f0d5ce0fdb3f4f88872647fc92d17008
Source dataset
uspto-grants-1990_01
Patent number
US04892576

Reaction notes

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