3,5-Dichloroaniline → HCID 20537572, compound

HRID 1155671Notes

Reaction equation

HRID 1155671 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]1[C:11](=[O:12])O[C:8](=[O:9])[CH2:7]1)=[O:4].[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[NH2:17]>O1CCCC1>[CH3:1][O:2][C:3]([NH:5][CH:6]1[CH2:7][C:8](=[O:9])[N:17]([C:16]2[CH:15]=[C:14]([Cl:13])[CH:20]=[C:19]([Cl:21])[CH:18]=2)[C:11]1=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 122813,5-DichloroanilineHCID 13944507HCID 13944507, compound

Product 1

HCID 20537572HCID 20537572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

12.9 g of N-methoxycarbonylaspartic anhydride are dissolved in 100 ml of tetrahydrofurane, and to this solution is added a solution of 12 g of 3,5-dichloroaniline in 50 ml of tetrahydrofurane. The reaction solution is stirred for 4 hours at 50° C. and then evaporated to dryness in vacuo. The residue is dissolved in 80 ml of acetic anhydride and then 2.5 g of sodium acetate are added and the solution is stirred for 11/2 hours at 80° C. After cooling to room temperature, the reaction mixture is poured into water and stirred vigorously for 1/2 hour. The mixture is extracted with ethyl acetate and the extracts are washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution, then dried over sodium sulfate, filtered and concentrated. Recrystallisation of the residue affords colourless crystals of the above compound with a melting point of 136°-138° C.

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutionThe residue is dissolved in 80 ml of acetic anhydride
  3. addition2.5 g of sodium acetate are added
  4. stirringthe solution is stirred for 11/2 hours at 80° C
  5. temperatureAfter cooling to room temperature
  6. additionthe reaction mixture is poured into water
  7. stirringstirred vigorously for 1/2 hour
  8. extractionThe mixture is extracted with ethyl acetate
  9. washthe extracts are washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customRecrystallisation of the residue
  14. customaffords colourless crystals of the above compound with a melting point of 136°-138° C.

Sources & evidence

ORD record
ord-30c6c0d9874244d9be29acba133425d1
Source dataset
uspto-grants-1982_06
Patent number
US04332816

Reaction notes

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