Triethylamine → [[[[(Benzhydryl)amino]thioxomethyl]methylamino]oxy]acetic acid

HRID 411973

Reaction equation

HRID 411973 reaction equation
[CH:1]([N:14]=[C:15]=[S:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:18][NH:19][O:20][CH2:21][C:22]([OH:24])=[O:23].C(N(CC)CC)C>C(Cl)(Cl)Cl.CCOCC>[CH:1]([NH:14][C:15]([N:19]([CH3:18])[O:20][CH2:21][C:22]([OH:24])=[O:23])=[S:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 520742Benzhydryl isothiocyanateHCID 85852466N-methyl aminooxy acetic acid hydrochloride

Product 1

HCID 12045032[[[[(Benzhydryl)amino]thioxomethyl]methylamino]oxy]acetic acidYield 93.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×

Procedure

A mixture of benzhydryl-isothiocyanate (13.75 g), N-methyl aminooxy acetic acid hydrochloride (8.6 g), triethylamine (16 g) and chloroform (200 mL) was heated at reflux for three hours, stirred at ambient temperature for one hour. The mixture was diluted with chloroform (200 mL) and washed with 2N HCl (2×300 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness to give a solid. The solid was stirred in ether (200 mL) and filtered to give 18.8 g of [[[[(benzhydryl)amino]thioxomethyl]methylamino]oxy]acetic acid as a white solid, m.p. 160-162° C. Mass spectrum (−FAB, [M−H]−) m/z 329. 1H-NMR (DMSO-d6; 400 MHz) δ13.55 (br s, 1H), 9.75 (d, 1H), 7.35-7.23 (m, 10H), 6.63 (d, 1H), 4.63 (s, 2H), and 3.42 ppm (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. washwashed with 2N HCl (2×300 mL)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customto give a solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-50183eaf6cae4780bfbc10c19dadfbdb
Source dataset
uspto-grants-2003_05
Patent number
US06562814B2

Linked notes

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