Tetrahydrofuran → 4-((3,4-Dichlorophenoxy)methyl)-2,5-difluoro-N-(methylsulfonyl)benzamide Diethylamine salt

HRID 508409Notes

Reaction equation

HRID 508409 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH2:6][C:7]1[C:15]([F:16])=[CH:14][C:10]([C:11]([NH2:13])=[O:12])=[C:9]([F:17])[CH:8]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:32][S:33](Cl)(=[O:35])=[O:34].[CH2:37]1COC[CH2:38]1>CCOC(C)=O>[CH2:37]([NH:13][CH2:11][CH3:10])[CH3:38].[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH2:6][C:7]1[C:15]([F:16])=[CH:14][C:10]([C:11]([NH:13][S:33]([CH3:32])(=[O:35])=[O:34])=[O:12])=[C:9]([F:17])[CH:8]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 31297Methanesulfonyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 666672344-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzamide

Product 1

HCID 866825554-((3,4-Dichlorophenoxy)methyl)-2,5-difluoro-N-(methylsulfonyl)benzamide Diethylamine salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4-((3,4-dichlorophenoxy)methyl)-2,5-difluorobenzamide (Preparation 24, 60 mg, 0.18 mmol) in THF (2 mL) was added a THF solution of lithium hexamethyldisilazide (1 M, 0.362 mL, 0.362 mmol) over 2 minutes. After stirring for 15-20 minutes, methanesulphonyl chloride (0.028 mL, 0.362 mmol) was added and the solution was stirred for 18 hours at room temperature. The reaction mixture was then diluted with EtOAc and washed twice with water. The organic layer was dried over sodium sulphate and evaporated to yield a yellow oil (65 mg), which was purified by preparative HPLC to yield the title compound.

Workup

  1. stirringthe solution was stirred for 18 hours at room temperature
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-a7e8aa6f166f4cfabc63cf03e31ef5aa
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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