Triethyl phosphite → 5H-[1,3]Thiazolo[2',3':2,3]imidazo[4,5-b]indole

HRID 1395565Notes

Reaction equation

HRID 1395565 reaction equation
[N:1]([C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[N:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.C(OP(OCC)OCC)C>C1(C)C=CC=CC=1>[S:7]1[C:6]2=[N:5][C:4]3[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:1][C:3]=3[N:10]2[CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 123187345-Nitroso-6-phenylimidazo[2,1-b][1,3]thiazole

Product 1

HCID 3673035H-[1,3]Thiazolo[2',3':2,3]imidazo[4,5-b]indoleYield 35.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8.5 grams of analytically pure 5-nitroso-6-phenylimidazo[2,1-b]thiazole (0.04 mole) and 10 ml. of triethylphosphite (0.05 mole) in 50 ml. of anhydrous toluene is refluxed for three hours with constant stirring and under a constant flow of dry nitrogen. The temperature of the oil bath is kept between 110° and 120° C. After cooling, the toluene and excess triethyl phosphite are removed by vacuum distillation at 0.2 Torr. The temperature of the oil bath is kept under 120° C. also during the distillation. The residue which is a thick oily liquid is kept over night at 0° C., during which time it solidifies. The solid is washed on a glass filter with cold carbon tetrachloride and then recrystallized twice from 2-propanol to yield three grams of 5H-thiazolo[2',3':2,3]imidazo[4,5-b]indole.

Workup

  1. customis kept between 110° and 120° C
  2. temperatureAfter cooling
  3. customthe toluene and excess triethyl phosphite are removed by vacuum distillation at 0.2 Torr
  4. distillationThe temperature of the oil bath is kept under 120° C. also during the distillation
  5. waitis kept over night at 0° C., during which time it
  6. washThe solid is washed on a glass
  7. filtrationfilter with cold carbon tetrachloride
  8. customrecrystallized twice from 2-propanol

Sources & evidence

ORD record
ord-a245175854c34704b6f72f24639da902
Source dataset
uspto-grants-1980_05
Patent number
US04204067

Reaction notes

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