Hydrochloric Acid → HCID 18357595, compound

HRID 1422143Notes

Reaction equation

HRID 1422143 reaction equation
[N:1]([CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C(O)=O.[ClH:46]>O1CCCC1.O.CO.CCOCC>[ClH:46].[O:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:4]([CH3:5])[NH2:1])=[N:13]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 11776TriphenylphosphineHCID 15550301HCID 15550301, compound

Product 1

HCID 18357595HCID 18357595, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent3×HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.64 g of 3-[2-(1-azidoethyl)-phenyl]-1,2-benzisoxazole in 10 ml of tetrahydrofuran and 0.1 ml of water was added 0.71 g of triphenyl phosphine. The solution was stirred for 2 days then diluted with 25 ml of water and the solution was extracted with two 50 ml portions of ether and the organic layers were dried over sodium sulfate then evaporated to give a pale yellow gum. This residue was dissolved in a small amount of methanol and 0.37 g of oxalic acid was added and warmed to dissolve. Ether was added and the white solid formed was separed and recrystalised from methanol-ether. To this solid was added 25 ml of a 5% aqueous solution of sodium carbonate and the solution extracted with 50 ml and then 25 ml of methylene chloride. The combined organic layers were washed with 25 ml water, 25 ml of brine then dried over sodium sulfate. Evaporation afforded a colourless oil which was dissolved in methanol and hydrogen chloride in methanol added until the solution was acidic. Evaporation and addition of ether yielded 2-(1,2-benzisoxazol-3-yl)-a-methyl-benzenemethanamine hydrochloride, melting at 229-236° C.

Workup

  1. extractionthe solution was extracted with two 50 ml portions of ether
  2. dry with materialthe organic layers were dried over sodium sulfate
  3. customthen evaporated
  4. customto give a pale yellow gum
  5. additionwas added
  6. temperaturewarmed to dissolve
  7. customthe white solid formed
  8. customrecrystalised from methanol-ether
  9. additionTo this solid was added 25 ml of a 5% aqueous solution of sodium carbonate
  10. extractionthe solution extracted with 50 ml
  11. washThe combined organic layers were washed with 25 ml water, 25 ml of brine
  12. dry with materialthen dried over sodium sulfate
  13. customEvaporation
  14. customafforded a colourless oil which
  15. customEvaporation and addition of ether

Sources & evidence

ORD record
ord-dd53376e924c4f03a880810acc3dae0d
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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