Pyridine → HCID 10669009, compound

HRID 1899092Notes

Reaction equation

HRID 1899092 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17][C:16]([NH2:18])=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:9][CH:8]=1.N1C=CC=CC=1>C(#N)C.O1CCCC1.C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17][C:16]([NH:18][C:2](=[O:3])[O:4][CH3:5])=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 104978555-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine

Product 1

HCID 10669009HCID 10669009, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Methyl chloroformate (0.23 ml) in acetonitrile (1 ml) was added dropwise to a stirred solution of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine (1.1 g) and pyridine (0.24 ml) in acetonitrile (8 ml) and tetrahydrofuran (10 ml) at -20° C. The mixture was stirred at 5° C. for 1 hour, diluted with ethyl acetate, washed with water, dried, and concentrated. The residue was purified by column chromatography on silica gel (30 g) eluting with a mixture of toluene and ethyl acetate (10:1). The product was recrystallized from ethanol to give pale red crystals of methyl N-{5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}carbamate (0.84 g).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (30 g)
  5. washeluting with a mixture of toluene and ethyl acetate (10:1)
  6. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-da1074229a504230af13b741f6c2f6d2
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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