N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 131716665, compound

HRID 1088721Notes

Reaction equation

HRID 1088721 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[NH2:23][CH2:24][CH:25]([C:27]1[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:32]=1)[OH:26]>CN(C=O)C>[C:25]([OH:26])(=[O:8])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1.[OH:38][C:30]1[CH:29]=[CH:28][C:27]([CH:25]([OH:26])[CH2:24][NH:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:32][C:31]=1[NH:33][S:34]([CH3:37])(=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 22161755HCID 22161755, compound

Product 1

HCID 131716665HCID 131716665, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-[(6-bromohexyl)oxy]butyl]quinoline (900 mg), N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide (800 mg) and DEA (0.52 ml) in DMF (50 ml) was heated at 100° for 4 h, cooled, and the solvent evaporated in vacuo. The residue was purified by FCC eluting with System A (39:10:1) and (34:15:1). A solution of the resulting product in methanol (10 ml) was treated with benzoic acid (61.3 mg), the solution evaporated in vacuo and triturated with dry ether (×2) to afford the title compound as a fawn powder (250 mg) m.p. 155°-157°.

Workup

  1. temperaturewas heated at 100° for 4 h
  2. temperaturecooled
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by FCC
  5. washeluting with System A (39:10:1) and (34:15:1)
  6. additionA solution of the resulting product in methanol (10 ml) was treated with benzoic acid (61.3 mg)
  7. customthe solution evaporated in vacuo
  8. customtriturated with dry ether (×2)

Sources & evidence

ORD record
ord-6bf5cd1989ec4f958ee870bbc5b5e568
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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