Triethylamine → HCID 14372494, compound

HRID 1723024Notes

Reaction equation

HRID 1723024 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[SH:12])[CH:5]=[CH:4][CH:3]=1.Cl[C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(N(CC)CC)C>CO>[N:15]1[CH:16]=[CH:17][CH:18]=[N:19][C:14]=1[S:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[N:2]=[CH:3][CH:4]=[CH:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 3082386Quinoline-8-thiol hydrochloride

Product 1

HCID 14372494HCID 14372494, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 210 mg. (1.06 m mole) of quinoline-8-thiol hydrochloride in 5 ml. of dry methanol was added 128 mg. (1.05 mmol) of 2-chloropyrimidine in 2 ml. of the same solvent followed by 0.148 ml (1 mmol) of dry triethylamine. The reaction mixture was allowed to stir at room temperature overnight followed by the removal of the methanol in vacuo. The residue was partitioned between a saturated sodium bicarbonate solution and ethyl acetate. The organic phase was separated, dried and concentrated. The residue was redissolved in chloroform and concentrated without heat. The residue was triturated with ethyl acetate, filtered and dried, 170 mg., m.p. 165°-168° C.

Workup

  1. customfollowed by the removal of the methanol in vacuo
  2. customThe residue was partitioned between a saturated sodium bicarbonate solution and ethyl acetate
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was redissolved in chloroform
  7. concentrationconcentrated
  8. temperaturewithout heat
  9. customThe residue was triturated with ethyl acetate
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-39115f5f66bf4fc7873ac3dea8bc284f
Source dataset
uspto-grants-1989_08
Patent number
US04859679

Reaction notes

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