(2Z)-3-Amino-2-butenenitrile → HCID 22768483, compound

HRID 1764455Notes

Reaction equation

HRID 1764455 reaction equation
[OH:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4](=O)[C:3]=1[CH:14]=O.[NH2:16]/[C:17](/[CH3:21])=[CH:18]\[C:19]#[N:20]>C(O)C>[CH3:21][C:17]1[N:16]=[CH:14][C:3]2[C:2](=[O:1])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][CH2:5][C:4]=2[C:18]=1[C:19]#[N:20]

Participants

4

Reactant 2

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 178519899HCID 178519899, compound

Product 1

HCID 22768483HCID 22768483, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 8.16 g (0.04 mole) of 2,3-dihydro-5-hydroxy-3-oxo-1-benzoxepin-4-carboxaldehyde, 4.92 g (0.06 mole) of 3-aminocrotononitrile and 50 ml of absolute ethanol was maintained at reflux for 10 min. and cooled. The separated crystals were filtered, washed with 10 ml ethanol and dried, wt. 5.2 g (52%); mp 124°-126°. Recrystallization was effected by dissolution in 75 ml of 50% dichloromethane-ethanol and removal, by distillation, of most of the dichloromethane. The pure product separated as tan crystals; wt. 2.9 g (29%), mp 126°-128°.

Workup

  1. temperatureat reflux for 10 min.
  2. temperaturecooled
  3. filtrationThe separated crystals were filtered
  4. washwashed with 10 ml ethanol
  5. customdried
  6. customRecrystallization
  7. dissolutionwas effected by dissolution in 75 ml of 50% dichloromethane-ethanol
  8. customremoval
  9. distillationby distillation
  10. customThe pure product separated as tan crystals

Sources & evidence

ORD record
ord-3bf28a8f3af74f489d0b4c62453644b2
Source dataset
uspto-grants-1978_09
Patent number
US04116966

Reaction notes

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