Formaldehyde → N-{4-[2-(4-{[(methyleneamino)oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide

HRID 2117876Notes

Reaction equation

HRID 2117876 reaction equation
[NH2:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1.[CH2:21]=O>CO>[CH2:21]=[N:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21914692N-[4-(2-{4-[(aminooxy)methyl]phenyl}ethyl)-1,3-thiazol-2-yl]acetamide

Product 1

HCID 21914698N-{4-[2-(4-{[(methyleneamino)oxy]methyl}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[4-(2-{4-[(Aminooxy)methyl]phenyl}ethyl)-1,3-thiazol-2-yl]acetamide (30 mg) prepared in a similar manner according to Production Example 16, 37% formaldehyde (8 μl) and dry methanol (1 ml) were combined under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 6 hours and concentrated in vacuo. The residue was purified by preparative silica gel column chromatography with chloroform/methanol (20:1) as an eluent, and triturated with ethyl ether to give N-{4-[2-(4-{[(methyleneamino)oxy]methyl}-phenyl)ethyl]-1,3-thiazol-2-yl}acetamide (20.9 mg) as a colorless solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative silica gel column chromatography with chloroform/methanol (20:1) as an eluent
  3. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-d3dd95dee68a4207a556949b82332f81
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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