Triethylamine → HCID 178463116, compound

HRID 1656869Notes

Reaction equation

HRID 1656869 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1Br.[CH2:14]([N:16]1[C:20]([OH:21])=[CH:19][CH:18]=[N:17]1)[CH3:15].C(N(CC)CC)C.[C]=O.[O:31]1CCOC[CH2:32]1>>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:32]([C:19]1[CH:18]=[N:17][N:16]([CH2:14][CH3:15])[C:20]=1[OH:21])=[O:31]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 14801178HCID 14801178, compoundHCID 178418331HCID 178418331, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 178463116HCID 178463116, compoundYield 43%

Conditions

Temperature
150 °C

Procedure

1.42 g of 2-chloro-4-methanesulfonyl-3-methylbromobenzene, 2.24 g of 1-ethyl-5-hydroxypyrazole, 10 ml of triethylamine, 0.175 g of dichloro(bistriphenylphosphine)palladium and 50 ml of dry 1,4-dioxane were charged into a 100 ml stainless steel autoclave equipped with a rotary stirrer, and the interior of the autoclave was substituted by carbon monoxide. Then, carbon monoxide was injected under a pressure of 20 kg/cm2. Then, the reaction temperature was raised to 150° C. under stirring, and the reaction was continued for 9 hours. The reaction mixture was left to cool and treated in the same manner as in Example 2-1 to obtain 0.60 g of the desired product (yield: 43%).

Workup

  1. customequipped with a rotary stirrer
  2. waitThe reaction mixture was left
  3. temperatureto cool
  4. additiontreated in the same manner as in Example 2-1

Sources & evidence

ORD record
ord-4d79d25b68504493a3467f664bad10a0
Source dataset
uspto-grants-1993_10
Patent number
USRE034423

Reaction notes

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