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

HRID 1087381Notes

Reaction equation

HRID 1087381 reaction equation
[NH:1]([CH:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=1)[CH3:4])[OH:2].C[Si]([N:23]=[C:24]=[O:25])(C)C.O>O1CCCC1>[CH:6]1[C:7]2[S:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:15][C:16]=2[CH:17]=[CH:18][C:5]=1[CH:3]([N:1]([OH:2])[C:24]([NH2:23])=[O:25])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 70696Trimethylsilyl isocyanateHCID 156610132-(1-Hydroxaminoethyl)phenoxathiin

Product 1

HCID 15661014N-[1-(Phenoxathiin-2-yl)ethyl]-N-hydroxy urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step 2 (250 mg, 0.965 mmol) in tetrahydrofuran (THF, 4 mL) there was added 85% trimethylsilyl isocyanate (196 mg, 1.45 mmol) and the solution was stirred at room temperature for 1 hour. Water (4 mL) was added, stirring was continued for 10 minutes, then the THF was evaporated; the residue was extracted twice with ether and the crude product obtained from evaporation of the extracts was crystallized from ether to afford the title compound as white crystals, m.p.: dec 155° C. with gassing.

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. customthe THF was evaporated
  4. extractionthe residue was extracted twice with ether
  5. customthe crude product obtained from evaporation of the extracts
  6. customwas crystallized from ether

Sources & evidence

ORD record
ord-8768f197ef424cc4ade8b5a1cbcf796c
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Reaction notes

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