Hydroxyamine hydrochloride → HCID 16222401, compound

HRID 2250463Notes

Reaction equation

HRID 2250463 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8](=S)[NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[Cl:17])=[O:11])=[CH:4][CH:3]=1.Cl.[NH2:22]O>O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[N:9]=[C:10]([C:12]3[S:13][CH:14]=[CH:15][C:16]=3[Cl:17])[O:11][N:22]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86593184HCID 86593184, compound

Product 1

HCID 16222401HCID 16222401, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of (3-chlorothiophene-2-carbonyl)-thiocarbamic acid O-(4-chloro-benzyl) ester (52.3 mg, 0.151 mg), hydroxylamine hydrochloride (20.7 mg, 0.298 mmol) was refluxed under argon for 1 h. The solution was cooled to room temperature, then water (6 mL) was added to precipitate the product, and the mixture was filtered. The filter cake was dissolved in dichloromethane, filtered through glass wool, and rotary evaporated to dryness. The product was recrystallized from dichloromethane/methanol to yield 3.1 mg (6.2%) of the title compound as a white solid. 1H NMR (CDCl3): 7.58 (d, J=5.7 Hz, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.37 (d, J=8.4 Hz, 1H), 7.10 (d, J=5.1 Hz, 1H), 5.36 (s, 2H).

Workup

  1. customto precipitate the product
  2. filtrationthe mixture was filtered
  3. dissolutionThe filter cake was dissolved in dichloromethane
  4. filtrationfiltered through glass wool
  5. customrotary evaporated to dryness
  6. customThe product was recrystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-18c2c022a56842329b1da1266d54f241
Source dataset
uspto-grants-2008_01
Patent number
US07317029B2

Reaction notes

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