Hydroxylamine → HCID 178460979, compound

HRID 2097609Notes

Reaction equation

HRID 2097609 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]([C:13]2[C:17]([CH2:18][O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[N:16][O:15][N:14]=2)SC)[CH:5]=[CH:6][C:7]=1[F:8].[NH2:30][OH:31]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:13]2[C:17]([CH2:18][O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[N:16][O:15][N:14]=2)=[N:30][OH:31])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58941961Methyl N-(3-chloro-4-fluorophenyl)-4-[(triisopropylsilyl)oxy]methyl-1,2,5-oxadiazole-3-carbimidothioate

Product 1

HCID 178460979HCID 178460979, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Methyl N-(3-chloro-4-fluorophenyl)-4-[(triisopropylsilyl)oxy]methyl-1,2,5-oxadiazole-3-carbimidothioate (3.0 g, 6.5 mmol) was dissolved in EtOH followed by addition of 4 mL hydroxylamine (99.9% in water solution). The reaction was stirred at 75° C. for 6 hrs and monitored by HPLC. The reaction was concentrated in vacuo to a yellow oil which was dissolved in chloroform and chromatographed on 120 g of silica gel eluting with (1:4), EtOAc/hexane. The product was concentrated to give the desired product as a white solid (2.57 g, 89%); MF═C19H28ClFN4O3Si; LCMS calculated for C19H29ClFN4O3Si(M+H)+: m/z=443.168.

Workup

  1. concentrationThe reaction was concentrated in vacuo to a yellow oil which
  2. dissolutionwas dissolved in chloroform
  3. customchromatographed on 120 g of silica gel eluting with (1:4), EtOAc/hexane
  4. concentrationThe product was concentrated

Sources & evidence

ORD record
ord-39b9e42e6be44a089a330fe732c64497
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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