Triethylamine → HCID 11826750, compound

HRID 2302141Notes

Reaction equation

HRID 2302141 reaction equation
[Cl:1][C:2]1[C:10]([CH2:11][O:12][C:13]2[N:17]([CH3:18])[N:16]=[CH:15][CH:14]=2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:23][C:24]1([CH3:32])[CH2:31][C:29](=[O:30])[CH2:28][C:26](=[O:27])[CH2:25]1.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:10]([CH2:11][O:12][C:13]2[N:17]([CH3:18])[N:16]=[CH:15][CH:14]=2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([CH:28]1[C:26](=[O:27])[CH2:25][C:24]([CH3:32])([CH3:23])[CH2:31][C:29]1=[O:30])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31358DimedoneHCID 11727658HCID 11727658, compound

Product 1

HCID 11826750HCID 11826750, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.0 g (2.9 mmol) of 2-chloro-3-[(1-methylpyrazol-5-yl)oxymethyl]-4-methylsulfonyl benzoic acid, 0.4 g (2.9 mmol) of dimedone and 0.72 g of N,N-dicyclohexylcarbodiimide in 50 ml of acetonitrile are heated at 40° C. for 4 h. After the reaction mixture has been stirred for 12 h at room temperature, 0.87 g of triethylamine and 0.57 g of trimethylsilylnitrile are added. Afterwards the reaction mixture is heated at 40° C. for 6 h, filtered, freed from the solvent under reduced pressure and the residue is purified over silica gel (eluent: toluene/tetrahydrofurane/acetic acid: 100/0/0→4/1/0.1). Yield: 0.25 g; m.p.82° C.

Workup

  1. temperatureAfterwards the reaction mixture is heated at 40° C. for 6 h
  2. filtrationfiltered
  3. customthe residue is purified over silica gel (eluent: toluene/tetrahydrofurane/acetic acid: 100/0/0→4/1/0.1)

Sources & evidence

ORD record
ord-785499ab663047cab9d50ae8947040a2
Source dataset
uspto-grants-2002_08
Patent number
US06432881B1

Reaction notes

Loading…