Pyridine → HCID 54001007, compound

HRID 1078614Notes

Reaction equation

HRID 1078614 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]2[S:16][N:15]3[C:17]([C:23]4[CH:32]=[CH:31][C:30]5[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=5[CH:24]=4)=[C:18]([CH2:20][CH2:21][OH:22])[S:19][C:14]3=[N:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].N1C=CC=CC=1>O>[C:33]([O:22][CH2:21][CH2:20][C:18]1[S:19][C:14]2[N:15]([S:16][C:12](=[N:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)(=[O:10])=[O:9])[N:13]=2)[C:17]=1[C:23]1[CH:32]=[CH:31][C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:24]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 53751483HCID 53751483, compound

Product 1

HCID 54001007HCID 54001007, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[2-(4-methylphenyl)sulfonylimino-6-(5,6,7,8-tetrahydro-2-naphthyl)-2H-thiazolo[3,2- b][1,2,4]thiadiazol-5-yl]ethanol (500 mg), acetic anhydride (1 ml) and pyridine (5 ml) was stirred at room temperature for i hour. The reaction mixture was added to water, and the resulting crystal was collected by filtration and washed with water. The obtained crystal was subjected to silica gel chromatography and eluted with ethyl acetate-hexane (1:1, v/v). The separating crystal was recrystallized from dichloromethane-methanol to yield 2-[2-(4-methylphenyl)sulfonylimino-6-(5,6,7,8-tetrahydro-2-naphthyl)-2H-thiazolo[3,2- b][1,2,4]thiadiazol-5-yl]ethyl acetate (355 mg, yield 65%) as a colorless needle.

Workup

  1. filtrationthe resulting crystal was collected by filtration
  2. washwashed with water
  3. washeluted with ethyl acetate-hexane (1:1
  4. customThe separating crystal was recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-c0dee57eadb946ad921e71d9a9ca8ff6
Source dataset
uspto-grants-1996_08
Patent number
US05550138

Reaction notes

Loading…