Water → N-[1-(8-Chlorophenoxathiin-2-yl)ethyl]-N-hydroxy urea

HRID 1087384Notes

Reaction equation

HRID 1087384 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([CH:16]([NH:18][OH:19])[CH3:17])=[CH:9][CH:10]=3)[S:5][C:4]=2[CH:3]=1.C[Si]([N:24]=[C:25]=[O:26])(C)C.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13]([O:12][C:11]3[CH:10]=[CH:9][C:8]([CH:16]([N:18]([OH:19])[C:25]([NH2:24])=[O:26])[CH3:17])=[CH:7][C:6]=3[S:5]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70696Trimethylsilyl isocyanateHCID 867449352-Chloro-8-(1-hydroxaminoethyl)phenoxathiin

Product 1

HCID 9949668N-[1-(8-Chlorophenoxathiin-2-yl)ethyl]-N-hydroxy urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step 1 (320 mg, 1.09 mmol) in THF (15 mL) there was added 85% trimethylsilyl isocyanate (295 mg, 2.18 mmol) and the mixture was stirred at room temperature for 45 minutes. After addition of water (5 mL) the mixture was stirred a further 10 minutes, then the THF was evaporated, the residual aqueous suspension diluted with water and filtered to afford the title compound as a white solid, m.p.: dec 173° C. (gassing).

Workup

  1. stirringwas stirred a further 10 minutes
  2. customthe THF was evaporated
  3. additionthe residual aqueous suspension diluted with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-181dc4399b1b4f4890ee01547aee4c42
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Reaction notes

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