Sodium Hydroxide → HCID 21428913, compound

HRID 437649Notes

Reaction equation

HRID 437649 reaction equation
[OH-].[Na+].Cl.Cl[CH2:5][CH2:6][NH2:7].C(=O)([O-])O.[Na+].[Cl:13][C:14]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=1[C:16](Cl)=[O:17]>ClC(Cl)Cl.O>[Cl:13][C:14]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=1[C:16]([N:7]1[CH2:6][CH2:5]1)=[O:17]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 179452,5-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 21428913HCID 21428913, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 21 parts of sodium hydroxide in 75 parts of water is added a solution of 29 parts of 2-chloroethanamine hydrochloride in 75 parts of water. The whole is stirred and heated for 10 minutes at 90° C. After cooling to 0° C, 19 parts of sodium hydrogen carbonate are added. While stirring vigorously, there is added dropwise, during a 45 minutes-period, a solution of 49 parts of 2,5-dichlorobenzoyl chloride in 75 parts of trichloromethane at a temperature below 0° C. Upon completion, stirring is continued for 30 minutes without cooling. The reaction mixture is warmed to 25° C and adjusted to pH 8 with a diluted sodium hydroxide solution. The product is extracted three times with trichloromethane. The combined extracts are washed three times with water, dried filtered and evaporated, yielding 62 parts of 1-(2,5-dichlorobenzoyl)-aziridine as a residue.

Workup

  1. temperatureAfter cooling to 0° C
  2. stirringWhile stirring vigorously
  3. additionthere is added dropwise, during a 45 minutes-period
  4. customat a temperature below 0° C
  5. stirringUpon completion, stirring
  6. temperaturewithout cooling
  7. temperatureThe reaction mixture is warmed to 25° C
  8. extractionThe product is extracted three times with trichloromethane
  9. washThe combined extracts are washed three times with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-9a87516bb6e8416c8549f90a3128939a
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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