Acetic Acid → HCID 22135224, compound

HRID 1826701Notes

Reaction equation

HRID 1826701 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(O)(=O)C.[C-:30]#[N:31].[K+]>O.ClCCl>[C:30]([C:2]1([CH3:1])[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][NH:3]1)#[N:31]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 22135225HCID 22135225, compound

Product 1

HCID 22135224HCID 22135224, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

In a 100 ml bomb tube made of stainless steel 10.12 g (30.0 millimoles) of 8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine and 50 ml of glacial acetic acid are weighed in. To the suspension at 15–20° C. 5.90 g (90.6 millimoles) of potassium cyanide are added within 5 minutes under cooling with icecold water. The bomb tube is sealed. The reaction mixture is stirred at 70° C. for 24 hours, cooled, stirred with 350 ml of dichloro methane and 350 ml of water and the layers are separated. The aqueous phase is extracted with 150 ml of dichloro methane, the organic phases are washed with 50 ml of water, dried over magnesium sulfate and evaporated. The residue is is crystallized from 100 ml of ether, filtered and washed with ether. Thus 10.40 g of the desired compound are obtained, yield 95%, mp.: 148–151° C.

Workup

  1. customat 15–20° C
  2. customThe bomb tube is sealed
  3. temperaturecooled
  4. customthe layers are separated
  5. extractionThe aqueous phase is extracted with 150 ml of dichloro methane
  6. washthe organic phases are washed with 50 ml of water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue is is crystallized from 100 ml of ether
  10. filtrationfiltered
  11. washwashed with ether

Sources & evidence

ORD record
ord-dd1371c4156f457db02ef0bbbcefb62c
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

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