Acetyl chloride → HCID 19742604, compound

HRID 2254517Notes

Reaction equation

HRID 2254517 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[NH:15][C:16](=[O:59])[C:17]1[CH:22]=[C:21]([NH:23][C:24](=[O:40])[CH:25]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:20]=[C:19]([NH:41][C:42](=[O:58])[CH:43]([CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:18]=1.[C:60](Cl)(=[O:62])[CH3:61]>C(Cl)Cl>[C:60]([C:11]1[C:10]([O:13][CH3:14])=[CH:9][C:8]([NH:15][C:16](=[O:59])[C:17]2[CH:18]=[C:19]([NH:41][C:42](=[O:58])[CH:43]([CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:20]=[C:21]([NH:23][C:24](=[O:40])[CH:25]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:22]=2)=[C:7]([O:6][CH3:5])[CH:12]=1)(=[O:62])[CH3:61]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 54168158HCID 54168158, compound

Product 1

HCID 19742604HCID 19742604, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1.6 l of methylene chloride were dissolved 168 ml of acetyl chloride and 315 g of aluminum chloride. While cooling the resulting solution with ice, 400 g of the compound (7-C) obtained above was added thereto. The mixture was stirred at room temperature for one hour. The reaction mixture was then poured into 10 l of ice water, and the mixture was stirred for one hour. The methylene chloride layer was separated, washed twice with water and concentrated under reduced pressure. To the concentrate, there was added 2 of acetonitrile. The mixture was heated under reflux for one hour and then left to stand to cool it to room temperature. The resulting crystal was recovered by filtration to obtain 383 g of the compound (7-D). Yield: 93%.

Workup

  1. customobtained
  2. additionabove was added
  3. stirringthe mixture was stirred for one hour
  4. customThe methylene chloride layer was separated
  5. washwashed twice with water
  6. concentrationconcentrated under reduced pressure
  7. additionTo the concentrate, there was added 2 of acetonitrile
  8. temperatureThe mixture was heated
  9. temperatureunder reflux for one hour
  10. waitleft
  11. temperatureto cool it to room temperature
  12. filtrationThe resulting crystal was recovered by filtration

Sources & evidence

ORD record
ord-2ff30e735bf24d9b897abb9af62d7060
Source dataset
uspto-grants-1993_08
Patent number
US05236803

Reaction notes

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