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Ethanethiol → HCID 19022702, compound

HRID 359711
Notes
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Reaction equation

HRID 359711 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].F[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH2:26][CH2:25][CH2:24][N:16]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:9][CH:8]=1>CN(C)C=O>[CH2:3]([S:5][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH2:26][CH2:25][CH2:24][N:16]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 122656SK&F 104351

Product 1

HCID 19022702HCID 19022702, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Sodium hydride (60%) (0.75 g, 19 mmol) was added to a solution of ethanethiol (2.1 ml, 1.7 g, 28 mmol) in N,N-dimethylformamide (15 ml) at 0° C. under an argon atmosphere. After stirring for 0.5 hours, 2-(4-fluorophenyl)-3-(4-pyridyl) 6,7-dihydro-[5H]-pyrrolo[1,2-a]-imidazole (3.5 g, 12.5 mmol) of Example 2 was added and the resulting solution heated to 95° C. for 6 hours. The cooled reaction mixture was evaporated under reduced pressure and the residue partitioned between IN aqueous sodium hydroxide and dichloromethane. The organic layer was washed successively with water and brine, dried (magnesium sulfate) and concentrated. The residue was chromatographed on silica gel eluting with 25:1 chloroform/methanol. Fractions containing product were combined, the solvent evaporated and the residue recrystallized from ethyl acetate to afford the titled compound; mp. 124-125° C. Anal. Calcd. for C19H19N3S: C,70 99; H, 5.96; N, 13.08; S, 9.97: Found: C, 70.99; H, 5.92; N, 13.07; S, 9.81.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated under reduced pressure
  3. customthe residue partitioned between IN aqueous sodium hydroxide and dichloromethane
  4. washThe organic layer was washed successively with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 25:1 chloroform/methanol
  8. additionFractions containing product
  9. customthe solvent evaporated
  10. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3418d27584c34caf8937f5f344e8da23
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05002941

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes