1-Bromopropane → HCID 23659148, compound

HRID 1968392Notes

Reaction equation

HRID 1968392 reaction equation
[S:1]1[C:5]([SH:6])=[N:4][N:3]=[C:2]1[SH:7].[H-].[Na+].Br[CH2:11][CH2:12][CH3:13].Cl[C:15]1[C:16]([C:21]#[N:22])=[N:17][CH:18]=[CH:19][N:20]=1>CN(C=O)C.C1C=CC=CC=1>[CH2:11]([S:6][C:5]1[S:1][C:2]([S:7][C:15]2[C:16]([C:21]#[N:22])=[N:17][CH:18]=[CH:19][N:20]=2)=[N:3][N:4]=1)[CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 78401-BromopropaneHCID 24758Sodium hydride2×HCID 2924653-Chloropyrazine-2-carbonitrileHCID 178418558HCID 178418558, compound

Product 1

HCID 23659148HCID 23659148, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,3,4-thiadiazole-2,5-dithiol (601 mg, 4.00 mmol) in DMF and benzene (6 ml, 1/1) was added NaH (60% dispersion in mineral oil, 176 mg, 4.40 mmol) slowly at 0° C. under nitrogen atmosphere. The resulting suspension was stirred at 0° C. for 15 minutes and then to the mixture was added bromopropane (492 mg, 2.00 mmol). The reaction was stirred at rt for 1 hr. To the reaction was added NaH (60% dispersion in mineral oil, 176 mg, 4.40 mmol) slowly at 0° C. and stirred for 15 minutes after addition. Then, 3-chloropyrazine-2-carbonitrile (557 mg, 4.00 mmol) was added to the mixture and the reaction was stirred at 50° C. under N2 overnight. The reaction was then cooled to room temperature and quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over MgSO4. Removal of solvent gave the crude product which was purified by chromatography to give the title compound as an off-white solid.

Workup

  1. stirringThe reaction was stirred at rt for 1 hr
  2. stirringstirred for 15 minutes
  3. additionafter addition
  4. stirringthe reaction was stirred at 50° C. under N2 overnight
  5. temperatureThe reaction was then cooled to room temperature
  6. customquenched with saturated NH4Cl solution
  7. extractionextracted with EtOAc
  8. washThe combined organic layers were washed with water, brine
  9. dry with materialdried over MgSO4
  10. customRemoval of solvent
  11. customgave the crude product which
  12. customwas purified by chromatography

Sources & evidence

ORD record
ord-7745298ff4ce4ea6ba9ae14e05c41c69
Source dataset
uspto-grants-2013_04
Patent number
US08426358B2

Reaction notes

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