Triethanolamine → HCID 13650108, compound

HRID 1761453Notes

Reaction equation

HRID 1761453 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].BrBr.N(CCO)(CCO)CCO.[NH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:27]([OH:29])=[O:28])=[N:23][C:24]=1[O:25][CH3:26].[Na]>CO.C(O)C.O.C(OCC)C>[C:1]([CH:2]1[CH2:3][N:17]1[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:27]([OH:29])=[O:28])=[N:23][C:24]=1[O:25][CH3:26])#[N:4]

Participants

10

Reactant 5

HCID 7618Triethanolamine2×HCID 7855AcrylonitrileHCID 24408BromineHCID 5360545SodiumHCID 13650103HCID 13650103, compound

Product 1

HCID 13650108HCID 13650108, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 887MethanolSolvent4×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2.33 g. (44 mmol) acrylonitrile are diluted with 1 ml. diethyl ether and, while stirring and illuminating, 7.05 g. (44 mmol) bromine are added dropwise thereto. The mixture is occasionally cooled in order to ensure that the internal temperature does not exceed 40° C. Stirring is continued for a further 5 minutes, the reaction mixture is diluted with 60 ml. methanol and a solution of 6.55 g. (44 mmol) triethanolamine in 60 ml. methanol is added dropwise thereto. After a further hour, there are simultaneously added dropwise thereto a solution of 6.55 g. (44 mmol) triethanolamine in 60 ml. methanol and a solution of 8 g. (44 mmol) 5-aminomethyl-6-methoxypyridine-2-carboxylic acid (m.p. 269°-270° C. (decomp.)) in 1 liter methanol/200 ml. water. The solution is left to stand for 24 hours, then evaporated substantially on a rotary evaporator and the aqueous solution adjusted with 2N hydrochloric acid to a pH of 4.5, followed by extracting continuously for 2 days with methylene chloride. The methylene chloride phase is then dried and evaporated to give 4.8 g. of an oil which is dissolved in 50 ml. ethanol. While cooling, the solution is mixed with a solution of 440 mg. sodium in 15 ml. ethanol. The sodium salt of 5-[(2-cyano-1-aziridinyl)-methyl]-6-methoxypyridine-2-carboxylic acid precipitates out and, after the addition of 100 ml. isopropanol, it is filtered off with suction, dried and washed with diethyl ether to give 3.7 g. (33% of theory) of the desired compound; m.p. 230°-232° C.

Workup

  1. customilluminating
  2. temperatureThe mixture is occasionally cooled in order
  3. customdoes not exceed 40° C
  4. additionthe reaction mixture is diluted with 60 ml
  5. waitAfter a further hour
  6. additionthere are simultaneously added dropwise
  7. waitThe solution is left
  8. waitto stand for 24 hours
  9. customevaporated substantially on a rotary evaporator
  10. extractionby extracting continuously for 2 days with methylene chloride
  11. dry with materialThe methylene chloride phase is then dried
  12. customevaporated
  13. customto give 4.8 g
  14. dissolutionof an oil which is dissolved in 50 ml
  15. temperatureWhile cooling
  16. additionthe solution is mixed with a solution of 440 mg
  17. customThe sodium salt of 5-[(2-cyano-1-aziridinyl)-methyl]-6-methoxypyridine-2-carboxylic acid precipitates out
  18. additionafter the addition of 100 ml
  19. filtrationisopropanol, it is filtered off with suction
  20. customdried
  21. washwashed with diethyl ether
  22. customto give 3.7 g

Sources & evidence

ORD record
ord-3ec18eb172df4fd98951f2714ab8fe12
Source dataset
uspto-grants-1989_05
Patent number
US04826858

Reaction notes

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