Triethylamine → 1-[3,5-Diethyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-pyrazol-4-ylmethyl]naphthalen-2-ol

HRID 725273Notes

Reaction equation

HRID 725273 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([Cl:25])[C:16]=1[N:26]1[C:30]([CH2:31][CH3:32])=[C:29]([CH2:33]O)[C:28]([CH2:35][CH3:36])=[N:27]1.C(N(CC)CC)C.CS(Cl)(=O)=O>CCOCC>[CH2:35]([C:28]1[C:29]([CH2:33][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][C:2]=2[OH:11])=[C:30]([CH2:31][CH3:32])[N:26]([C:16]2[C:15]([Cl:14])=[CH:20][C:19]([C:21]([F:22])([F:24])[F:23])=[CH:18][C:17]=2[Cl:25])[N:27]=1)[CH3:36]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 86632-NaphtholHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 21837337[1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl]methanol

Product 1

HCID 675535871-[3,5-Diethyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-pyrazol-4-ylmethyl]naphthalen-2-olYield 29%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 303 mg (2.1 mmol) of 2-naphthol in 5 mL of dry ether was treated with 50 mg (2.1 mmol) of sodium hydride and the mixture was stirred for 15 minutes. A solution of 368 mg (1.0 mmol) of the compound of step C in 5 mL of dry ether and 126 mg (0.174 mL, 1.22 mmol) of triethylamine was cooled to 0° C. and treated with 114 mg (0.077 mL, 1.0 mmol) of methanesulfonyl chloride. Triethylamine hydrochloride was removed by filtration and the filtrate was added to the above suspension of sodium 2-naphthoxide and the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was then partitioned between water and ether and the organic extracts were dried and evaporated to give the desired product in 29% yield. 1H-NMR (CDCl3) δ1.00 (3H, t, J=7), 1.20 (3H, t, J=7), 2.44 (2H, q, J=7), 4.58 (2H, s), 6.96-7.84 (8H, m).

Workup

  1. customTriethylamine hydrochloride was removed by filtration
  2. additionthe filtrate was added to the above suspension of sodium 2-naphthoxide
  3. stirringthe reaction mixture was stirred at room temperature for 12 hours
  4. customThe reaction mixture was then partitioned between water and ether
  5. customthe organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-6251fcbee52440acbaccee62e2395c4e
Source dataset
uspto-grants-1998_01
Patent number
US05705646

Reaction notes

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