Triethylamine → HCID 20337755, compound

HRID 1395632Notes

Reaction equation

HRID 1395632 reaction equation
[NH2:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[N:4]=[N:3]1.[Br:12][CH2:13][CH2:14][C:15](Cl)=[O:16].C(N(CC)CC)C>C1C=CC=CC=1>[Br:12][CH2:13][CH2:14][C:15]([NH:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[N:4]=[N:3]1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84944Propanoyl chloride, 3-bromo-HCID 203377545-Methyl-1H-benzotriazol-1-amine

Product 1

HCID 20337755HCID 20337755, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 14.8 g (0.1 mol of 1-amino-5-methyl benztriazole in 200 ml of anhydrous benzene was placed under a nitrogen atmosphere and, over a period of 30 minutes, a solution of 18.9 g (0.11 mol) of β-bromopropionyl chloride in 25 ml of anhydrous benzene and 10.1 g (0.10 mol) of triethylamine were simultaneously added to the solution while stirring the latter. The addition was so made that the amount of acid chloride added was always greater than the amount of amine. The temperature of the mixture rose to above 40° C. Stirring was then continued for 1 hour without application of heat and was continued for a further hour with heating to 60° C. following by stirring for two further hours without application of heat. The organic phase was then poured off from a greasy deposit in the reaction vessel and was washed with water. The deposit was taken up in chloroform and was also washed with water. The organic phases obtained were dried over sodium sulphate, combined and completely concentrated by evaporation. 24 G of the intermediate product, 1-(β-bromopropionylamino)-5-methyl benztriazole were obtained as residue in the form of a frothy resin.

Workup

  1. additionThe addition
  2. additionadded
  3. customrose to above 40° C
  4. stirringStirring
  5. temperatureof heat
  6. waitwas continued for a further hour
  7. stirringby stirring for two further hours without application
  8. temperatureof heat
  9. additionThe organic phase was then poured off from a greasy deposit in the reaction vessel
  10. washwas washed with water
  11. washwas also washed with water
  12. customThe organic phases obtained
  13. dry with materialwere dried over sodium sulphate
  14. concentrationcompletely concentrated by evaporation

Sources & evidence

ORD record
ord-fd08de06e2664029827a078ca5bfe283
Source dataset
uspto-grants-1980_05
Patent number
US04204998

Reaction notes

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