Acetyl chloride → HCID 69595737, compound

HRID 1826702Notes

Reaction equation

HRID 1826702 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:7]1([CH3:31])[CH2:13][C:12]2[CH:14]=[C:15]3[O:20][CH2:19][O:18][C:16]3=[CH:17][C:11]=2[C:10]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([CH3:30])[CH:22]=2)=[N:9][NH:8]1)#[N:6]>>[C:1]([N:8]1[C:7]([C:5]#[N:6])([CH3:31])[CH2:13][C:12]2[CH:14]=[C:15]3[O:20][CH2:19][O:18][C:16]3=[CH:17][C:11]=2[C:10]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([CH3:30])[CH:22]=2)=[N:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 22135224HCID 22135224, compound

Product 1

HCID 69595737HCID 69595737, compoundYield 67%

Procedure

To 60 ml of acetyl chloride 9.11 g (25.0 millimoles) of (±)-8-cyano-7,8-dihydro-8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine are added at 15° C. under stirring. The suspension formed turns into a solution within 5 minutes, but after a further period of 5 minutes a suspension is re-formed. The reaction mixture is stirred at 25° C. for 6 days, whereupon it is evaporated in vacuo. To the residue 90 ml of water are added and the mixture is stirred under cooling with icecold water for half an hour. The precipitated crystals are filtered and washed with icecold water. The crude product is crystallized from 150 ml of acetonitrile. The crystals are filtered, washed with acetonitrile and ether and dried. Thus 6.84 g of the desired compound are obtained, yield 67%, mp.: 253–255° C.

Workup

  1. customThe suspension formed turns into a solution within 5 minutes
  2. customafter a further period of 5 minutes a suspension is re-formed
  3. stirringThe reaction mixture is stirred at 25° C. for 6 days, whereupon it
  4. customis evaporated in vacuo
  5. additionTo the residue 90 ml of water are added
  6. stirringthe mixture is stirred
  7. temperatureunder cooling with icecold water for half an hour
  8. filtrationThe precipitated crystals are filtered
  9. washwashed with icecold water
  10. customThe crude product is crystallized from 150 ml of acetonitrile
  11. filtrationThe crystals are filtered
  12. washwashed with acetonitrile and ether
  13. customdried

Sources & evidence

ORD record
ord-f4123d95290148e7baecba789dfc621d
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

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