Hydrochloric Acid → 2-(1-Hydroxaminoethyl)phenoxathiin

HRID 1087380

Reaction equation

HRID 1087380 reaction equation
[N:1](=[C: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].B.N1C=CC=CC=1.Cl>C(O)C>[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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5151822-(1-Hydroximinoethyl)phenoxathiinHCID 2723995Borane;pyridine

Product 1

HCID 156610132-(1-Hydroxaminoethyl)phenoxathiinYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The oxime from Step 1 (450 mg, 1.75 mmol) was suspended in ethanol (9 mL) and, at 0° C., there was added pyridine-borane (325 mg, 3.5 mmol) and 4M ethanolic hydrogen chloride (HCl) (1.33 mL, 5.32 mmol). The mixture was stirred at 0° C. for 20 minutes, then at room temperature for 1 hour. The ethanol was evaporated and the residue partitioned between water and ether. The aqueous portion was basified with 1N aqueous sodium hydroxide and extracted twice with ether. Drying of the ether and evaporation afforded the title product (408 mg) as an oil which slowly became a white solid, m.p.: 64°-67° C.

Workup

  1. waitat room temperature for 1 hour
  2. customThe ethanol was evaporated
  3. customthe residue partitioned between water and ether
  4. extractionextracted twice with ether
  5. dry with materialDrying of the ether and evaporation

Sources & evidence

ORD record
ord-e653b95f47a446148c1ae41f2403e257
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Linked notes

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