Ammonia → HCID 54143499, compound

HRID 2295510Notes

Reaction equation

HRID 2295510 reaction equation
[CH2:1]([O:10][N:11]=[C:12]([CH3:16])[C:13](O)=[O:14])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(Cl)([Cl:19])=O.N.C(ON=C(C)C(N)=O)C=CC1C=CC=CC=1>O.C(Cl)(Cl)Cl>[CH2:1]([O:10][N:11]=[C:12]([CH3:16])[C:13]([Cl:19])=[O:14])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 53856608HCID 53856608, compoundHCID 53967269HCID 53967269, compound

Product 1

HCID 54143499HCID 54143499, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

2-(Cinnamyloxyimino)-propionyl chloride is prepared from 4.38 g. (20 mmol) 2-(cinnamyloxyimino)-propionic acid and 3.57 g. (30 mmol) thionyl chloride in the manner described in Example 6. The crude acid chloride is dissolved in 20 ml. chloroform and added, while stirring, to an ice-cooled solution of ammonia in 40 ml. chloroform. The reaction mixture is left to stand overnight at ambient temperature and then shaken up with 100 ml. water. Subsequently, the organic phase is first washed with 0.5 N hydrochloric acid, then with a saturated aqueous solution of sodium bicarbonate and dried over anhydrous sodium sulphate and evaporated in a vacuum. The residue is recrystallized from a mixture of ethyl acetate and ligroin to give 2.9 g. (66% of theory) 2-(cinnamyloxyimino)-propionamide; m.p. 120°-121° C.

Workup

  1. waitThe reaction mixture is left
  2. washSubsequently, the organic phase is first washed with 0.5 N hydrochloric acid
  3. dry with materialwith a saturated aqueous solution of sodium bicarbonate and dried over anhydrous sodium sulphate
  4. customevaporated in a vacuum
  5. customThe residue is recrystallized from a mixture of ethyl acetate and ligroin
  6. customto give 2.9 g

Sources & evidence

ORD record
ord-001da949a15f484a8af87b00d6b445b7
Source dataset
uspto-grants-1984_01
Patent number
US04425360

Reaction notes

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