Acetyl chloride → HCID 21320431, compound

HRID 262256Notes

Reaction equation

HRID 262256 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-f9ed6053feff4f908ff943445a803088
Source dataset
uspto-grants-1979_05
Patent number
US04153731

Reaction notes

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