Hydrochloric Acid → HCID 86630501, compound

HRID 1520405Notes

Reaction equation

HRID 1520405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:32])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([S:20]CC4C=CC=CC=4)=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH2:33].[ClH:34].Cl[O-:36].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:32])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([Cl:34])(=[O:36])=[O:33])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665760Sodium HypochloriteHCID 66777044HCID 66777044, compound2×

Product 1

HCID 86630501HCID 86630501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(3,5-dichlorophenyl)-4,5-dihydro-3-[3-methyl-4-[(phenylmethyl)-thio]phenyl]-5-(trifluoromethyl)isoxazole (i.e. the product from Step A) (2.88 g, 5.8 mmol) in methylene chloride (50 mL) and water (50 mL) was added concentrated hydrochloride acid (1.92 mL, 20 mmol) at 5° C., followed by dropwise addition of sodium hypochlorite (6.15%—Clorox® brand) (50 mL). The reaction mixture was then stirred vigorously for 1 h. The reaction mixture was added to methylene chloride (100 mL) and washed with water (2×100 mL). The organic extracts were dried (MgSO4) and concentrated to afford the title product as an oil (3.1 g).

Workup

  1. washwashed with water (2×100 mL)
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e3ae24572b7247bc942b276ab620695a
Source dataset
uspto-grants-2015_07
Patent number
US09073910B2

Reaction notes

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