Methanol → HCID 14372494, compound

HRID 1382728Notes

Reaction equation

HRID 1382728 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.CO.Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1>C(N(CC)CC)C>[N:17]1[CH:18]=[CH:19][CH:20]=[N:21][C:16]=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 887MethanolHCID 744042-ChloropyrimidineHCID 3082386Quinoline-8-thiol hydrochloride

Product 1

HCID 14372494HCID 14372494, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 210 mg. (1.06 m mole) of quinoline-8-thiolhydrochloride in 5 ml. of dry methanol was added 128 mg. (1.05 m mole) of 2-chloropyrimidine in 2 ml. of the same solvent followed by 148 ul (1 m mole) 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-5d7bb971accd468f8a0d46d84e762586
Source dataset
uspto-grants-1989_02
Patent number
US04808591

Reaction notes

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