Isopropylamine → HCID 70416795, compound

HRID 622222Notes

Reaction equation

HRID 622222 reaction equation
[O:1]1[C:7]2[C:2]1=[CH:3][C:4](OC)=[C:5]([C:8]1[C:12]3SC=C[C:11]=3[O:10][N:9]=1)[CH:6]=2.[CH2:18]([CH:20]1[O:22][CH2:21]1)Br.OC1C=CC(C2[C:34]3[S:35]C=C[C:33]=3ON=2)=CC=1.[CH:38]([NH2:41])([CH3:40])[CH3:39].[C:42]([O-:49])(=[O:48])/[CH:43]=[CH:44]\[C:45]([O-:47])=[O:46]>C(OCC)(=O)C.CCOCC.C(O)C>[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]\[C:45]([OH:47])=[O:46].[CH3:39][CH:38]([NH:41][CH2:18][CH:20]([OH:22])[CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:33]=[CH:34][S:35][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1)[CH3:40]

Participants

8

Reactant 5

HCID 6363IsopropylamineHCID 18430EpibromohydrinHCID 5288227Maleate(2-)HCID 86742417HCID 86742417, compoundHCID 135856719HCID 135856719, compound

Product 1

HCID 70416795HCID 70416795, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

A mixture of 3 g of 3-(4-epoxymethoxyphenyl)thieno[2,3-d]isoxazole (prepared from epibromohydrin and 3-(4-hydroxyphenyl)thieno[2,3-d]isoxazole in substantially the same manner as Example 5), 5 ml of absolute ethanol and 5 ml of isopropylamine was refluxed for three hours. The excess amine and ethanol were removed under a reduced pressure, leaving a residue. The crude product was extracted into 400 ml of ethyl acetate/ether (1:1) and shaken with ice-cold (10%) hydrochloric acid. The aqueous solution was separated and basified with concentrated NH3 to liberate the product. Extraction with ethyl acetate/ether (1:1) followed by washing and drying yielded a colorless solid weighing 2.8 g. The free base was converted to crystalline maleate in ethyl acetate/ether and recrystallized from methanol/ether to afford plates, m.p. 153°-155° C.

Workup

  1. temperaturewas refluxed for three hours
  2. customThe excess amine and ethanol were removed under a reduced pressure
  3. customleaving a residue
  4. extractionThe crude product was extracted into 400 ml of ethyl acetate/ether (1:1)
  5. customThe aqueous solution was separated
  6. extractionExtraction with ethyl acetate/ether (1:1)
  7. washby washing
  8. customdrying
  9. customyielded a colorless solid
  10. customrecrystallized from methanol/ether
  11. customto afford plates, m.p. 153°-155° C.

Sources & evidence

ORD record
ord-47ef0b355b0e4fea8f5edd56c69a2ef4
Source dataset
uspto-grants-1988_09
Patent number
US04769472

Reaction notes

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