Hydroxylamine → HCID 53720242, compound

HRID 596773Notes

Reaction equation

HRID 596773 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]#[N:9].[NH2:10][OH:11]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8](=[N:10][OH:11])[NH2:9]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 1111403-(2-Thienyl)-2-propenenitrile

Product 1

HCID 53720242HCID 53720242, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

β-(Thien-2-yl) acrylonitrile (2.78 g.) was dissolved in dry methanol (60 ml.) and treated with a solution of hydroxylamine in methanol (60 ml.) (prepared by dissolving hydroxylamine hydrochloride (6 g.), in methanol (60 ml.) and neutralising with sodium methoxide in methanol). The solution was refluxed for 6 hr. and left overnight to cool. Evaporation in vacuo left a brown oil which was dissolved in chloroform and washed with water (10 ml.). The chloroform solution was evaporated to dryness leaving the crude amidoxime, 2.76 g. (80%). Recrystallisation from aqueous methanol gave β-(thien-2-yl) acrylamidoxime, m.p. 92° , λmax. (EtOH) 306 nm, (ε 20070) (Found: C, 49.7; H, 4.7; N, 16.8; S, 18.7. C7H8N2OS requires C, 50.0; H, 4.8; N, 16.7; S, 19.05%).

Workup

  1. temperatureThe solution was refluxed for 6 hr
  2. temperatureto cool
  3. customEvaporation in vacuo
  4. waitleft a brown oil which
  5. dissolutionwas dissolved in chloroform
  6. washwashed with water (10 ml.)
  7. customThe chloroform solution was evaporated to dryness
  8. customleaving the crude amidoxime, 2.76 g
  9. customRecrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-4d066e01f1634419864303f1555bc3ac
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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