Triethylamine → 2-(Benzyloxycarbonylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole

HRID 65034Notes

Reaction equation

HRID 65034 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH2:15])=[S:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br[CH:18]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=O.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[S:14][C:18]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[N:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756641N-Benzyloxycarbonylglycine thioamideHCID 114633362-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide

Product 1

HCID 155958722-(Benzyloxycarbonylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazoleYield 60.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 40 ml of acetonitrile was dissolved 1.12 g of benzyloxycarbonylaminothioacetamide. In the solution was suspended 2.0 g of 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone hydrobromide. To the suspension was added while stirring 0.8 ml of triethylamine. The mixture was stirred for 2 hours under reflux. The resultant was left standing for cooling, then the solvent was evaporated off. To the residue was added a saturated aqueous solution of sodium hydrogen carbonate. The mixture was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried and, then, the solvent was evaporated off. The residue was recrystallized from ethyl acetate-isopropylether to give 1.3 g (yield 56%) of 2-(benzyloxycarbonylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole, m.p. 93°-94° C.

Workup

  1. additionTo the suspension was added
  2. temperatureunder reflux
  3. waitThe resultant was left
  4. temperaturefor cooling
  5. customthe solvent was evaporated off
  6. additionTo the residue was added a saturated aqueous solution of sodium hydrogen carbonate
  7. extractionThe mixture was subjected to extraction with ethyl acetate
  8. washThe extract solution was washed with water
  9. customdried
  10. customthe solvent was evaporated off
  11. customThe residue was recrystallized from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-5fdaf02e511442198dc152b965d76be3
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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