Cyanogen Bromide → HCID 20311570, compound

HRID 2420360Notes

Reaction equation

HRID 2420360 reaction equation
[NH:1]([CH2:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].[N:17]#[C:18]Br>C(O)C>[NH:17]=[C:18]1[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:8][C:9](=[NH:11])[O:10]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516893Potassium BicarbonateHCID 153703192-(Phenylamino)acetamide

Product 1

HCID 20311570HCID 20311570, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 3.75 g. of anilinoacetamide, 2.5 g. of potassium bicarbonate and 50 ml. of ethanol was added rapidly 2.7 g. of cyanogen bromide in 20 ml. of ethanol. The reaction mixture was heated to reflux. After heating overnight and cooling, a small amount of precipitate was in the flask. This was filtered and the ethanolic filtrate shown to be slightly acidic. The ethanol filtrate was concentrated down to dryness leaving a solid which was washed with ethanol. The yield of product, m.p. 117°-9° C., was 3.9 g. (88%). The mass spectrum of the product gives a parent ion at m/e 175. This product is used to prepare intermediate III.

Workup

  1. additionTo a mixture of 3.75 g
  2. temperatureThe reaction mixture was heated to reflux
  3. temperatureAfter heating overnight
  4. temperaturecooling
  5. filtrationThis was filtered
  6. concentrationThe ethanol filtrate was concentrated down to dryness
  7. customleaving a solid which
  8. washwas washed with ethanol
  9. customThe mass spectrum of the product gives a parent ion at m/e 175

Sources & evidence

ORD record
ord-f189126fe418449f9944debf2dc4c410
Source dataset
uspto-grants-1978_08
Patent number
US04110445

Reaction notes

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