Acrylonitrile → HCID 13061753, compound

HRID 1075297Notes

Reaction equation

HRID 1075297 reaction equation
COC(=O)N(C(C)C)C=CC(C)=C.C(#N)C=C.[CH:18]([N:21]([CH:26]1[CH:31]=[C:30]([CH3:32])[CH2:29][CH2:28][CH:27]1[C:33]#[N:34])[C:22]([O:24][CH3:25])=[O:23])([CH3:20])[CH3:19].[S]>>[CH:18]([N:21]([C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[C:33]#[N:34])[C:22]([O:24][CH3:25])=[O:23])([CH3:20])[CH3:19]

Participants

5

Reactant 4

HCID 7855AcrylonitrileHCID 5362487SulfurHCID 13590129HCID 13590129, compoundHCID 53684414HCID 53684414, compound

Product 1

HCID 13061753HCID 13061753, compound

Procedure

915 g N-isopropyl-N-(3-methyl-1,3-butadienyl)-carbamic acid methyl ester are heated without a solvent to 120° C. and 345 g acrylonitrile added dropwise. After completion of the addition the mixture is stirred for 1 hour at 140°. The resulting 2-(N-isopropyl-N-carbomethoxyamino)-4-methyl-3-cyclohexene-nitrile is heated at 200° and treated over a period of 2 hours portionwise with 386 g powdered sulphur. The reaction mixture is then stirred for 2 hours at 205° C. The resulting mixture is distilled under high vacuum at 110°-120° (0,1 torr), recrystallisation of the residue from benzine fraction yields the title product m.p. 100°-101°.

Workup

  1. additionAfter completion of the addition the mixture
  2. additiontreated over a period of 2 hours portionwise with 386 g
  3. stirringThe reaction mixture is then stirred for 2 hours at 205° C
  4. distillationThe resulting mixture is distilled under high vacuum at 110°-120°
  5. custom(0,1 torr), recrystallisation of the residue from benzine fraction

Sources & evidence

ORD record
ord-59a0077eb1674edab6e2cb5e4a47a175
Source dataset
uspto-grants-1983_07
Patent number
US04395550

Reaction notes

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