Methylamine → HCID 57980012, compound

HRID 1867555Notes

Reaction equation

HRID 1867555 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]3[C:21](=[O:22])[CH2:20][O:19][C:18]3=[O:23])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:24][NH2:25]>O1CCCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18](=[O:23])[O:19][CH2:20][C:21]([NH:25][CH3:24])=[O:22])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 67528120HCID 67528120, compound

Product 1

HCID 57980012HCID 57980012, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.46 g (1.39 mmol) of 3-(2-(4-[(4-chlorophenyl)oxy]phenyl)ethyl)-1,3-oxazolidine-2,4-dione, prepared in step 14.2., is redissolved in a mixture of 3 ml of tetrahydrofuran and 6 ml of methanol. 3 ml of a 2M solution of methylamine (6 mmol) in tetrahydrofuran are added. The mixture is left to react at ambient temperature overnight and then 2 g of silica are added and the mixture is evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 98/2 then 96/4 and 94/6 mixture of dichloromethane and methanol. The product is recrystallized from a mixture of ethyl acetate and diisopropyl ether, to give 0.40 g of product in the form of a white powder.

Workup

  1. waitThe mixture is left
  2. customto react at ambient temperature overnight
  3. addition2 g of silica are added
  4. customthe mixture is evaporated to dryness
  5. customThe residue is purified by chromatography on silica gel
  6. washeluting with a 98/2
  7. addition96/4 and 94/6 mixture of dichloromethane and methanol
  8. customThe product is recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-8537d009dc5648e69fe633e86c1d6071
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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