Methylhydrazine → 4-[(Aminooxy)methyl]-2-(hex-1-yn-1-yl)-1,3-thiazole

HRID 2039683Notes

Reaction equation

HRID 2039683 reaction equation
[C:1]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][O:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[N:11]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].CNN>O1CCCC1>[NH2:14][O:13][CH2:12][C:10]1[N:11]=[C:7]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])[S:8][CH:9]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 674260462-{[2-(hex-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 674252094-[(Aminooxy)methyl]-2-(hex-1-yn-1-yl)-1,3-thiazoleYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[2-(hex-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1H-isoindole-1,3(2H)-dione (13.6 g, 40.1 mmol) in tetrahydrofuran (250 mL) was added methylhydrazine (3.69 g, 80.1 mmol) dropwise. After stirring 20 h at room temperature, the reaction mixture was concentrated in vacuo, diluted with ethyl acetate, washed with water and the organic layer drid (MgSO4) and concentrated in vacuo. Purification on silica gel afforded 4-[(aminooxy)methyl]-2-(hex-1-yn-1-yl)-1,3-thiazole as a colourless oil [8.15 g, yield 94%; HPLC/MS: m/z=211 (M+H); log P(HCOOH)=1.76].

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. concentrationthe organic layer drid (MgSO4) and concentrated in vacuo
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-24cda93e0fd5435eb71832abb805a278
Source dataset
uspto-grants-2013_11
Patent number
US08580799B2

Reaction notes

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