Sodium hydride → HCID 11722538, compound

HRID 275366Notes

Reaction equation

HRID 275366 reaction equation
[H-].[Na+].C([NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19](=O)[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)(=O)C1C=CC=CC=1.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>O1CCCC1>[Cl:18][C:16]1[CH:17]=[C:12]2[C:13]([C:19]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:29]([C:30]([O:32][CH3:33])=[O:31])[NH:11]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10247519HCID 10247519, compound

Product 1

HCID 11722538HCID 11722538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of a 50% sodium hydride suspension in mineral oil (52.5 g) (which was extracted with dry heptane) and dry tetrahydrofuran (250 ml) was added a solution of N-benzoyl 5-chloro-2-(4-fluorobenzoyl)aniline (129 g) in dry tetrahydrofuran (500 ml) during 0.5 h at 20° C. (ice bath). After 1 h methyl 2-bromoacetate (101 ml) was added during 0.5 h at 20° C. (ice bath) and the mixture was stirred for another 1 hour. The solvents were evaporated in vacuo. The remaining oil was diluted with methanol (250 ml) and 5.4M sodium methoxide in methanol (670 ml) was added carefully. After 1 h at room temperature the solvents were evaporated in vacuo and water (0.5 l) was added. The thus obtained mixture was extracted with ethyl acetate (2×0.75 l) and the combined organic phases were washed with brine and dried (Na2SO4). Evaporation of the solvents in vacuo afforded the title compound, which was purified by column chromatography on silica gel (eluted with ethyl acetate/heptane 1:3) and crystallized from heptane. Yield: 33 g, mp 172°-183° C.

Workup

  1. customThe solvents were evaporated in vacuo
  2. additionThe remaining oil was diluted with methanol (250 ml) and 5.4M sodium methoxide in methanol (670 ml)
  3. additionwas added carefully
  4. customAfter 1 h at room temperature the solvents were evaporated in vacuo and water (0.5 l)
  5. additionwas added
  6. extractionThe thus obtained mixture was extracted with ethyl acetate (2×0.75 l)
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-655a045ef4b74124a6dc721908892f17
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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