Hydrochloric Acid → HCID 20567881, compound

HRID 1733294Notes

Reaction equation

HRID 1733294 reaction equation
[CH3:1][N:2]([CH3:12])[CH2:3][CH2:4][NH:5][C:6]1[CH:10]=[C:9]([CH3:11])[O:8][N:7]=1.C(N(CC)CC)C.[CH3:20][N:21]([CH3:25])[C:22]([Cl:24])=[O:23].Cl>CCOCC.C(O)C.C1C=CC=CC=1>[ClH:24].[CH3:20][N:21]([CH3:25])[C:22]([N:5]([CH2:4][CH2:3][N:2]([CH3:12])[CH3:1])[C:6]1[CH:10]=[C:9]([CH3:11])[O:8][N:7]=1)=[O:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 20567878HCID 20567878, compound

Product 1

HCID 20567881HCID 20567881, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 8.46 g. (0.05 mole) of N,N-dimethyl-N'-(5-methyl-3-isoxazolyl)-1,2-ethane-diamine in 75 ml. of benzene (dry) is added 5.6 g. (0.055 mole) of triethylamine followed by 5.9 g. (0.055 mole) of dimethylcarbamoyl chloride. The solution is slowly heated to 85° C. and stirred at 80°-85° C. for 6 hours. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The reddish liquid residue is taken up in 125 ml. of hexane and filtered through charcoal which is then washed well with ether. Concentration of the combined filtrates in vacuo gives 10.3 g. of a reddish liquid. This is dissolved in 5 ml. of ethanol, cooled in ice and 6.8 ml. of 6 N ethanolic hydrochloric acid is added. Addition of ether precipitates the mono hydrochloride salt (11.5 g.) as an "off white" solid, which is filtered and dried in vacuo. The salt is recrystallized by dissolving it in 15 ml. of hot ethanol, adding ether with stirring to incipient cloudiness (35-40 ml.), and slowly diluting with another 100-110 ml. of ether when crystallization is well underway. Filtration affords 9.9 g. of white solid, m.p. 142.5°-143.5° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. filtrationof hexane and filtered through charcoal which
  4. washis then washed well with ether
  5. customConcentration of the combined filtrates in vacuo gives 10.3 g
  6. dissolutionThis is dissolved in 5 ml
  7. customprecipitates the mono hydrochloride salt (11.5 g.) as an "off white" solid, which
  8. filtrationis filtered
  9. customdried in vacuo
  10. customThe salt is recrystallized
  11. dissolutionby dissolving it in 15 ml
  12. additionof hot ethanol, adding ether
  13. stirringwith stirring to incipient cloudiness (35-40 ml.)
  14. additionslowly diluting with another 100-110 ml
  15. customof ether when crystallization
  16. filtrationFiltration
  17. customaffords 9.9 g

Sources & evidence

ORD record
ord-8591a4bbeb834aa2ad80b6f19128aeea
Source dataset
uspto-grants-1980_12
Patent number
US04241072

Reaction notes

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