Dimethylamine → HCID 70474692, compound

HRID 638557Notes

Reaction equation

HRID 638557 reaction equation
CC[O:3][CH2:4][CH3:5].CO.[CH3:8][NH:9][CH3:10].Br[CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:19])[CH:14]=1.CC[O:29][C:30]([CH3:32])=[O:31]>CCOCC>[C:4]([OH:3])(=[O:17])/[CH:5]=[CH:32]\[C:30]([OH:29])=[O:31].[CH3:8][N:9]([CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:19])[CH:14]=1)[CH3:10]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 20252673HCID 20252673, compoundHCID 21864698Diethyl ether methanol

Product 1

HCID 70474692HCID 70474692, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 50% Et2O/MeOH mixture (250 ml) was saturated with dimethylamine gas and cooled in an ice-bath. To this was added a solution of 4.5 g of (5-bromomethylisoxazol-3-yl)-4-fluorophenylmethanone in 25 ml of Et2O. The resulting solution was allowed to warm to room temperature and stirred for two days. The methanol was evaporated in vacuo to give an residue, which was dissolved in 500 ml of EtOAc. The solution was washed with water until neutral and with saturated NaCl, dried over Na2SO4, and evaporated to give 3.5 g of an oil which solidified on standing.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe methanol was evaporated in vacuo
  3. customto give an residue, which
  4. washThe solution was washed with water until neutral and with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-eebfdca702c04387b0c96455fe36726b
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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