Cyanogen Bromide → HCID 20311575, compound

HRID 2420361Notes

Reaction equation

HRID 2420361 reaction equation
[NH:1]([CH2:8][C:9]([NH2:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](=[O:15])(O)[O-].[K+].[N:17]#CBr.N1CCN=C1>C(O)C.C(O)C.CO>[C:2]1([N:1]2[CH2:8][C:9]([NH2:11])=[N:17][C:12]2=[O:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10476Cyanogen BromideHCID 681562-ImidazolineHCID 516893Potassium BicarbonateHCID 153703192-(Phenylamino)acetamide

Product 1

HCID 20311575HCID 20311575, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

To a mixture of 3.75 g. of anilinoacetamide, 2.5 g. of potassium bicarbonate and 40 ml. of ethanol was added dropwise 2.7 g. of cyanogen bromide in 20 ml. of ethanol. This mixture was heated to reflux overnight. On cooling, a light tan precipitate formed in the flask. The precipitate was filtered, washed with ethanol, water, and dried overnight. The yield of product, m.p. 277°-9° C. was 3.3 g. (75%). The mass spectrum of the compound gave a parent ion at m/e 175. An analytical sample was prepared by recrystallization from ethanol-methanol, m.p. 280°-2° C. In this case the ethanol filtrate was basic at the conclusion of the reaction leading to formation of the imidazoline in situ. This product is used in Examples 10 and 11.

Workup

  1. additionTo a mixture of 3.75 g
  2. temperatureThis mixture was heated
  3. temperatureto reflux overnight
  4. temperatureOn cooling
  5. customa light tan precipitate formed in the flask
  6. filtrationThe precipitate was filtered
  7. washwashed with ethanol, water
  8. customdried overnight
  9. customThe mass spectrum of the compound gave a parent ion at m/e 175

Sources & evidence

ORD record
ord-c26a41d200f5439db3afe0f420d07d1c
Source dataset
uspto-grants-1978_08
Patent number
US04110445

Reaction notes

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