Triethylamine → HCID 21391851, compound

HRID 461998Notes

Reaction equation

HRID 461998 reaction equation
[CH2:1]([S:3][C:4]1[S:5][C:6]([C:9]([OH:11])=O)=[CH:7][N:8]=1)[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:25]12[CH:31]([CH2:32][CH2:33][NH2:34])[CH:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2>O1CCCC1>[CH2:1]([S:3][C:4]1[S:5][C:6]([C:9]([NH:34][CH2:33][CH2:32][CH:31]2[CH:25]3[CH2:30][CH2:29][CH:28]2[CH2:27][CH2:26]3)=[O:11])=[CH:7][N:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 213919102-Ethylthio-5-carboxythiazoleHCID 21391941HCID 21391941, compound

Product 1

HCID 21391851HCID 21391851, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

In this preparation 0.1 mole of 2-ethylthio-5-carboxythiazole is dissolved in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, and 0.1 moles of triethylamine is added and the resulting mixture cooled to -30° C. 0.1 Mole of ethylchloroformate is then added dropwise with stirring and the resulting mixture allowed to warm to 0° C. The mixture is then stirred for ten minutes, then cooled to -30° C and 0.11 moles of 2-(bicyclo[2.2.1]hept-7-yl)ethylamine in 50 ml. of tetrahydrofuran added dropwise. The mixture is allowed to warm to room temperature (about 20° C), poured in 500 ml. of ethyl acetate, washed with water, then washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The mixture is then filtered and the resulting filtrate evaporated under vacuum yielding 2-ethylthio-5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]-thiazole as a solid, which is then further purified by recrystallization from ethyl acetate.

Workup

  1. dissolutionis dissolved in 300 ml
  2. temperatureto warm to 0° C
  3. stirringThe mixture is then stirred for ten minutes
  4. temperaturecooled to -30° C
  5. temperatureto warm to room temperature (about 20° C)
  6. additionpoured in 500 ml
  7. washof ethyl acetate, washed with water
  8. washwashed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe mixture is then filtered
  11. customthe resulting filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-24e4c78a942d4cc49e3096ba2807cd27
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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