Triethylamine → HCID 18977950, compound

HRID 2392996Notes

Reaction equation

HRID 2392996 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:24]([O:25][CH3:26])=[C:23]([S:27][CH3:28])[CH:22]=[CH:21][C:10]=1[C:11]([C:13]1[CH:14]=[N:15][O:16][C:17]=1[CH:18]1[CH2:20][CH2:19]1)=[O:12]>ClCCl>[Br:8][C:9]1[C:24]([O:25][CH3:26])=[C:23]([S:27][CH3:28])[CH:22]=[CH:21][C:10]=1[C:11](=[O:12])[CH:13]([C:14]#[N:15])[C:17]([CH:18]1[CH2:20][CH2:19]1)=[O:16]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54000764HCID 54000764, compound

Product 1

HCID 18977950HCID 18977950, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.58 g) was added to a stirred solution of 4(2-bromo-3-methoxy-4-methylsulphenylbenzoyl)-5-cyclopropylisoxazole (2.0 g) in dichloromethane and the mixture was stirred at room temperature for 3 hours. The mixture was evaporated to dryness and the residue triturated with ether and filtered. The solid was re-dissolved in dichloromethane and washed with hydrochloric acid (2M). The organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue triturated with ether and filtered to give 1-(2-bromo-3-methoxy-4-methylsulphenylphenyl)-2-cyano-3-cyclopropylpropan-1,3-dione (COMPOUND 661, 1.33 g) as a white solid, m.p. 128°-129° C.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue triturated with ether
  3. filtrationfiltered
  4. dissolutionThe solid was re-dissolved in dichloromethane
  5. washwashed with hydrochloric acid (2M)
  6. washThe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue triturated with ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-dec9d0fba3b5499398a72c0c74434699
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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