Hydroxylamine → HCID 178460981, compound

HRID 2097641Notes

Reaction equation

HRID 2097641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]([C:13]2[N:14]=[N:15][S:16][C:17]=2[CH2:18][O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])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[N:14]=[N:15][S:16][C:17]=2[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:30][OH:31])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58941825HCID 58941825, compound

Product 1

HCID 178460981HCID 178460981, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl N-(3-chloro-4-fluorophenyl)-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thiadiazole-4-carbimidothioate (90 mg, 0.0002 mol) was dissolved in EtOH (2 mL) followed by addition of hydroxylamine (116 μL, 0.00190 mol) (50% by wt, 99.9% in water solution). The reaction was stirred at 60° C. for 4 h and overnight at room temperature. The reaction was evaporated and purified by flash chromatography to give the desired product (85 mg, 98%). 1H NMR (400 MHz, CDCl3): δ 7.32 (s, 1H), 7.25 (s, 1H), 6.90 (m, 2H), 6.62 (m, 2H), 5.17 (s, 2H), 1.05 (m, 21H). MF=C19H28ClFN4O2SSi; LCMS calculated for C19H29ClFN4O2SSi (M+H)+: m/z=459.2.

Workup

  1. customThe reaction was evaporated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-fc946d1d1be94d32a67c4651fcf814cf
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

Loading…