3,4-Dichlorobenzyl alcohol → HCID 71616386, compound

HRID 1525644Notes

Reaction equation

HRID 1525644 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][OH:6].[H-].[Na+].[CH3:13][N:14]([CH3:30])[S:15]([NH:18][C:19](=[O:29])[C:20]1[CH:25]=[C:24]([F:26])[C:23](F)=[CH:22][C:21]=1[F:28])(=[O:17])=[O:16]>O1CCCC1.CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][O:6][C:23]1[C:24]([F:26])=[CH:25][C:20]([C:19]([NH:18][S:15]([N:14]([CH3:30])[CH3:13])(=[O:17])=[O:16])=[O:29])=[C:21]([F:28])[CH:22]=1

Participants

6

Reactant 3

HCID 157283,4-Dichlorobenzyl alcoholHCID 24758Sodium hydrideHCID 89618925HCID 89618925, compound

Product 1

HCID 71616386HCID 71616386, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dichlorobenzyl alcohol (157 mg, 0.884 mmol) in tetrahydrofuran (3 mL) was added sodium hydride (60% dispersion in oil, 37 mg, 0.92 mmol). The reaction was stirred at room temperature for 45 minutes and heated to 55° C. for 30 minutes. The reaction mixture was cooled to room temperature and concentrated in vacuo. To the residue was added a solution of N-[(dimethylamino)sulfonyl]-2,4,5-trifluorobenzamide (Preparation 3, 100 mg, 0.354 mmol) in dimethyl sulfoxide (2 mL). The reaction mixture was stirred at room temperature for 3 hours and then partitioned between aqueous 2M hydrochloric acid (5 mL) and ethyl acetate (10 mL). The organic phase was separated and washed with a saturated aqueous solution of sodium chloride (10 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was triturated with diethyl ether, filtered and dried in vacuo to afford the title compound as a white solid (56 mg, 29%).

Workup

  1. temperatureheated to 55° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. stirringThe reaction mixture was stirred at room temperature for 3 hours
  5. custompartitioned between aqueous 2M hydrochloric acid (5 mL) and ethyl acetate (10 mL)
  6. customThe organic phase was separated
  7. washwashed with a saturated aqueous solution of sodium chloride (10 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude material was triturated with diethyl ether
  12. filtrationfiltered
  13. customdried in vacuo

Sources & evidence

ORD record
ord-c3b4090642ff4900a6f7fdc966754c23
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

Loading…