Acetyl chloride → HCID 22135230, compound

HRID 1826700Notes

Reaction equation

HRID 1826700 reaction equation
[CH3:1][C:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[N:4][N:3]=1.[C:26](Cl)(=[O:28])[CH3:27]>>[C:26]([N:3]1[C:2]([CH3:1])=[CH:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[N:4]1)(=[O:28])[CH3:27]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 22135225HCID 22135225, compound

Product 1

HCID 22135230HCID 22135230, compoundYield 69%

Procedure

A mixture of 3.37 g (10.0 millimoles) of 8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine and 25 ml acetyl chloride is stirred under boiling for 3 hours, whereupon the acid chloride is distilled off in vacuo. The residue is taken up in 100 ml of dichloro methane, washed with 50 ml of a saturated sodium carbonate solution and 50 ml of water. The organic phase is dried over magnesium sulfate and evaporated in vacuo. The crude product obtained is recrystallized from 50 ml of acetonitrile. Thus 2.62 g of the desired compound are obtained, yield 69%, mp.: 115–116° C.

Workup

  1. distillationis distilled off in vacuo
  2. washwashed with 50 ml of a saturated sodium carbonate solution and 50 ml of water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude product obtained
  6. customis recrystallized from 50 ml of acetonitrile

Sources & evidence

ORD record
ord-f8e96d605ba447cfb0965e4c82db2005
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

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