Hydrochloric Acid → HCID 18977986, compound

HRID 2392998Notes

Reaction equation

HRID 2392998 reaction equation
C(N(CC)CC)C.[CH:8]1([C:11]2[O:15][N:14]=[CH:13][C:12]=2[C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([S:24][CH3:25])[CH:18]=2)[CH2:10][CH2:9]1.Cl>ClCCl>[C:13]([CH:12]([C:11]([CH:8]1[CH2:9][CH2:10]1)=[O:15])[C:16]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([S:24][CH3:25])[CH:18]=1)=[O:26])#[N:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 18977973HCID 18977973, compound

Product 1

HCID 18977986HCID 18977986, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.5 g) was added to a solution of 5-cyclopropyl-4-(4-methyl-3-methylsulphenylbenzoyl)isoxazole (0.66 g) in dichloromethane. The mixture was stirred at room temperature overnight. Further triethylamine (0.2 g) was added and the mixture was stirred for a further 24 hours. Hydrochloric acid (2M) was added and the layers were separated. The organic layer was washed with aqueous sodium chloride solution, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 2-cyano-3-cyclopropyl-1-(4-methyl-3-methylsulphenylphenyl)propan-1,3-dione (COMPOUND 665, 0.12 g) as an orange gum which solidified, m.p. 64.7°-67.9° C.

Workup

  1. stirringthe mixture was stirred for a further 24 hours
  2. customthe layers were separated
  3. washThe organic layer was washed with aqueous sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f7a0e238c6b04ce48cb9de7e95c33119
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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