Hydroxyamine hydrochloride → HCID 49823922, compound

HRID 1108114Notes

Reaction equation

HRID 1108114 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([CH:26]=O)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.Cl.[NH2:29][OH:30]>CO.N1C=CC=CC=1>[OH:30][N:29]=[CH:26][C:20]1([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([S:13][C:10]3[CH:11]=[CH:12][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:8][CH:9]=3)[CH:15]=2)[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18786390HCID 18786390, compound

Product 1

HCID 49823922HCID 49823922, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

4-[3-[4-(2-Methylimidazol-1-yl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde (178 mg, 0.47 mmol) and hydroxylamine hydrochloride (210 mg, 3 mmol) were dissolved in a mixture of methanol (4 ml) and pyridine (1 ml) and the reaction mixture was stirred for 5 h at ambient temperature. Volatiles were removed in vacuo and the resultant residue was diluted with 0.1 N aqueous NaOH (20 ml) and extracted with ethyl acetate (30 ml×3). The combined organic layers were washed with water (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo. The residual solids were recrystallized from ethyl acetate to afford 130 mg (70%) of the titled compound as white solids.

Workup

  1. customVolatiles were removed in vacuo
  2. additionthe resultant residue was diluted with 0.1 N aqueous NaOH (20 ml)
  3. extractionextracted with ethyl acetate (30 ml×3)
  4. washThe combined organic layers were washed with water (50 ml) and brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residual solids were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-005c0d158951461d97c2f252643c60e7
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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