Pyridine → 5-Morpholinosulfonamido-1-naphthol

HRID 1390089

Reaction equation

HRID 1390089 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].N1C=CC=CC=1.[O:19]1[CH2:24][CH2:23][N:22]([S:25](Cl)(=[O:27])=[O:26])[CH2:21][CH2:20]1>C(#N)C>[O:19]1[CH2:24][CH2:23][N:22]([S:25]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[C:7]3[OH:12])(=[O:27])=[O:26])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 657465-Amino-1-naphtholHCID 12798265Morpholine-4-sulfonyl chloride

Product 1

HCID 202948755-Morpholinosulfonamido-1-naphthol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4.8 g. of 5-amino-1-naphthol in 210 ml. of acetonitrile were added 2.5 ml. of pyridine and a mixture of 75 ml. of acetonitrile and 5.6 g. of morpholinosulfonyl chloride was added dropwise thereto under stirring and ice-cooling. Stirring was continued at room temperature for 2 hours and reaction was conducted at 40° C. for 1 hour. The mixture was concentrated and the residue was added to about 150 ml. of water containing 3 ml. of conc. hydrochloric acid. The precipitate thus separated was recovered by filtration, washed with water and then dried to give 6.7 g. of the desired product with m.p. 220°-223° C. (with dec.).

Workup

  1. temperatureice-cooling
  2. stirringStirring
  3. customreaction
  4. waitwas conducted at 40° C. for 1 hour
  5. concentrationThe mixture was concentrated
  6. additionthe residue was added to about 150 ml
  7. customThe precipitate thus separated
  8. filtrationwas recovered by filtration
  9. washwashed with water
  10. customdried
  11. customto give 6.7 g

Sources & evidence

ORD record
ord-041a96044e89404187fade2fbd457a2f
Source dataset
uspto-grants-1981_01
Patent number
US04247629

Linked notes

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