Hydrochloric Acid → HCID 69194039, compound

HRID 1370271Notes

Reaction equation

HRID 1370271 reaction equation
O[CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C@H:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1.[ClH:29].O=S(Cl)[Cl:32]>C(Cl)Cl>[ClH:32].[Cl:29][CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C@H:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 69195542HCID 69195542, compound

Product 1

HCID 69194039HCID 69194039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

) (5S)-4,5-dihydro-N-[4-(hydroxyphenylmethyl)phenyl]-3-(3-pyridinyl)-5-isoxazolecarboxamide (0.027 mol) was suspended in CH2Cl2 (250 ml). HCl, gas (excess) was allowed to bubble through the suspension for 2 minutes. SOCl2 (0.097 mol) was added dropwise and the reaction mixture was stirred and refluxed for 4 hours. The solvent was evaporated under reduced pressure. Toluene was added and azeotroped on the rotary evaporator (2×). The residue was stirred in toluene. The precipitate was filtered off, washed with toluene and dried, yielding 11.5 g (100% crude yield) of (5S)-N-[4-(chlorophenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide monohydrochloride (compound 500).

Workup

  1. customto bubble through the suspension for 2 minutes
  2. temperaturerefluxed for 4 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionToluene was added
  5. customazeotroped on the rotary evaporator (2×)
  6. stirringThe residue was stirred in toluene
  7. filtrationThe precipitate was filtered off
  8. washwashed with toluene
  9. customdried

Sources & evidence

ORD record
ord-14a228edc6634a6a9b241e2fbbf4f280
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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