Sodium Hydroxide → HCID 9819591, compound

HRID 622742Notes

Reaction equation

HRID 622742 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1.[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH2:20])[CH3:16].[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][C:5]([C:6]([NH:20][CH2:19][CH2:18][N:17]([CH2:21][CH3:22])[CH2:15][CH3:16])=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 60993N,N-DiethylethylenediamineHCID 542055134-Chloro-5-cyano-2-methoxybenzoyl chloride

Product 1

HCID 9819591HCID 9819591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While stirring under nitrogen, at minus 30°, a solution of 23 g (0.1 mol) of 4-chloro-5-cyano-2-methoxybenzoic acid chloride in 70 ml of methylene chloride is added dropwise to a solution of 11.6 g (0.1 mol) of 2-diethylaminoethylamine in 100 ml of methylene chloride. The resulting white suspension is then stirred at room temperature for 15 hours, 105 ml (0.105 mol) of 1M sodium hydroxide solution are then added dropwise thereto and the whole is stirred until 2 distinct layers have formed and then separated in a separating funnel, and the aqueous phase is again extracted by shaking with 50 ml of methylene chloride. The combined organic phases are dried over magnesium sulphate and filtered, 150 ml of cyclohexane are added and methylene chloride is distilled off until the distillation temperature is 70°. After cooling, the base that has crystallised out is filtered off with suction and then washed with cyclohexane. After drying, 4-chloro-5-cyano-N-(2-diethylaminoethyl)- 2-methoxybenzamide having a melting point of 104°-105° is obtained.

Workup

  1. stirringThe resulting white suspension is then stirred at room temperature for 15 hours
  2. stirringthe whole is stirred until 2 distinct layers
  3. customhave formed
  4. customseparated in a separating funnel
  5. extractionthe aqueous phase is again extracted
  6. stirringby shaking with 50 ml of methylene chloride
  7. dry with materialThe combined organic phases are dried over magnesium sulphate
  8. filtrationfiltered
  9. addition150 ml of cyclohexane are added
  10. distillationmethylene chloride is distilled off until the distillation temperature
  11. customis 70°
  12. temperatureAfter cooling
  13. customthe base that has crystallised out
  14. filtrationis filtered off with suction
  15. washwashed with cyclohexane
  16. customAfter drying

Sources & evidence

ORD record
ord-17bec4cda76b472787b399148ce75dac
Source dataset
uspto-grants-1988_09
Patent number
US04772630

Reaction notes

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