Acetyl chloride → HCID 21320431, compound

HRID 839383Notes

Reaction equation

HRID 839383 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[O:5]([C:12]1[CH:28]=[CH:27][C:15]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)C(C)C)C>C1C=CC=CC=1>[O:5]([C:12]1[CH:28]=[CH:27][C:15]([N:16]([C:1](=[O:3])[CH3:2])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 21320435HCID 21320435, compound

Product 1

HCID 21320431HCID 21320431, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

3.2 ml of acetyl chloride dissolved in 10 ml of anhydrous benzene is added dropwise at 0° - 5° C in the course of one hour, with stirring, to a solution of 12.7 g of 4-phenoxy-N-(3,4-methylenedioxybenzyl)-aniline and 6 g of N-ethyl-diisopropylamine in 100 ml of anhydrous benzene. The whole is subsequently heated to room temperature and stirred for a further 8 hours. The precipitated N-ethyl-diisopropylamine-hydrochloride is separated by filtration; the filtrate is washed with 10% sodium carbonate solution and then with water. After drying of the organic phase by means of sodium sulphate, the benzene is distilled off in vacuo, and the residue recrystallised in hexane to obtain 4-phenoxy-N-acetyl-N-(3,4-methylenedioxybenzyl)-aniline, M.P. 75°- 76° C.

Workup

  1. additionis added dropwise at 0° - 5° C in the course of one hour
  2. customThe precipitated N-ethyl-diisopropylamine-hydrochloride is separated by filtration
  3. washthe filtrate is washed with 10% sodium carbonate solution
  4. dry with materialAfter drying of the organic phase by means of sodium sulphate
  5. distillationthe benzene is distilled off in vacuo
  6. customthe residue recrystallised in hexane

Sources & evidence

ORD record
ord-48d6dbca74e34a6a874274a1759d6e37
Source dataset
uspto-grants-1978_06
Patent number
US04094989

Reaction notes

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