Hydroxyamine hydrochloride → 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine

HRID 875195Notes

Reaction equation

HRID 875195 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)=O)[S:4][N:3]=1.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)=[N:16][OH:17])[S:4][N:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66887208(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methanone

Product 1

HCID 1363312531-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimineYield 110.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methanone (3.00 g, 10.2 mmol) and hydroxylamine hydrochloride (844 mg, 25.5 mmol) in pyridine (30 mL) was stirred 4 h at 50° C. then overnight at room temperature. After removal of the solvent in vacuo, addition of water (50 mL) and extraction with ethyl acetate (3×40 mL), the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified on silica gel to afford 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine [3.15 g, yield 99%; HPLC/MS: m/z=279 (M+H); log P(HCOOH)=3.04].

Workup

  1. customovernight
  2. customat room temperature
  3. customAfter removal of the solvent
  4. additionin vacuo, addition of water (50 mL) and extraction with ethyl acetate (3×40 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-bb5cbf12df3f4dd4abd6b0cf13dc6647
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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