Sodium hydride → HCID 14621629, compound

HRID 1905357Notes

Reaction equation

HRID 1905357 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([NH:15][C:16](=[O:19])[O:17][CH3:18])=[O:14])=[CH:8][CH:7]=[CH:6]2.[H-].[Na+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([C:20]([F:22])([F:21])[F:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([N:15]([C:16]([O:17][CH3:18])=[O:19])[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:14])=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 14621639HCID 14621639, compound

Product 1

HCID 14621629HCID 14621629, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[[6-Methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, methyl ester (2.2 g, 6.72 mmol) was added to a suspension of sodium hydride (60% in oil, 0.29 g, 7.25 mmol) in tetrahydrofuran (anhydrous, 150 mL) and the mixture stirred for 1.5 hours at 20° C. tert-Butyl bromoacetate (1.20 mL, 7.40 mmol) was added and the resultant solution was stirred for 20 hours at 20° C. The solvent was evaporated and the residual solid triturated with hexanes (3×20 mL), to yield the pure product (2.1 g, 71.2%) as a white crystalline solid.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residual solid triturated with hexanes (3×20 mL)

Sources & evidence

ORD record
ord-5efed54b5c4145df808f9000a218d4b3
Source dataset
uspto-grants-1989_06
Patent number
US04843062

Reaction notes

Loading…