Hydrochloric Acid → Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

HRID 1594432Notes

Reaction equation

HRID 1594432 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:3]=1[CH3:14].[CH3:15][S:16]SC.N(OCCCC)=O.Cl>[Cu].O>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5]([S:16][CH3:15])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 12232Dimethyl DisulfideHCID 9813747Benzenamine, 4-bromo-2-(4,5-dihydro-3-isoxazolyl)-3-methyl-

Product 1

HCID 9860657Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-Yield 89%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

114.7 g (0.45 mol) of 4-bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline, 857 mg of copper powder and 1000 ml of dimethyl disulfide are initially charged. Over a period of one hour, 49.2 g of n-butyl nitrite are metered in at 58-65° C., and the mixture is stirred until the reaction has gone to completion (about 1-3 hours). At 20-25° C., 130 ml of conc. hydrochloric acid are added, and the mixture is stirred for 20-30 minutes. 130 ml of water are added, and the phases are then separated. Washing is repeated twice. The organic phase is concentrated, giving 114.4 g of product (yield: 89%).

Workup

  1. customare metered in at 58-65° C.
  2. customhas gone to completion (about 1-3 hours)
  3. stirringthe mixture is stirred for 20-30 minutes
  4. customthe phases are then separated
  5. washWashing
  6. concentrationThe organic phase is concentrated

Sources & evidence

ORD record
ord-3b1f5bcda6a0442b853ec39c2c5bc90a
Source dataset
uspto-grants-2007_11
Patent number
US07301034B2

Reaction notes

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