Methylamine → HCID 59128611, compound

HRID 1990705Notes

Reaction equation

HRID 1990705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[CH2:19][O:18][C:17]3=[O:22])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:23][NH2:24]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:22])[O:18][CH2:19][C:20]([NH:24][CH3:23])=[O:21])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 67399614HCID 67399614, compound

Product 1

HCID 59128611HCID 59128611, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.6 g (1.87 mmol) of 3-{3-[3-(4-chlorophenyl)isoxazol-5-yl]propyl}-1,3-oxazolidine-2,4-dione, prepared in stage 4.2., is dissolved in a mixture of 8 ml of tetrahydrofuran and of 15 ml of methanol. 2.8 ml of a 2M solution of methylamine (5.6 mmol) in tetrahydrofuran are added. Reaction is allowed to take place at ambient temperature overnight and then the mixture is evaporated. The residue is purified by chromatography on silica gel, elution being carried out with a 98/2 and then 95/5 and 90/10 mixture of dichloromethane and of methanol. The product is recrystallized from a mixture of ethyl acetate and of methanol to produce 0.49 g (1.4 mmol) of white crystals.

Workup

  1. customReaction
  2. customat ambient temperature
  3. customovernight
  4. customthe mixture is evaporated
  5. customThe residue is purified by chromatography on silica gel, elution
  6. addition95/5 and 90/10 mixture of dichloromethane
  7. customThe product is recrystallized from a mixture of ethyl acetate and of methanol

Sources & evidence

ORD record
ord-1779428d73934d5e87e456b6e9cb305f
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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