Triethylamine → HCID 9948873, compound

HRID 1531023Notes

Reaction equation

HRID 1531023 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:21])([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11](O)=[O:12])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:29][OH:30].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.C1COCC1.O>[OH:30][NH:29][C:11](=[O:12])[C:10]([S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 443297Hydroxyamine hydrochlorideHCID 15484979HCID 15484979, compound

Product 1

HCID 9948873HCID 9948873, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionic acid (0.5 g, 1.65 mmol) and DMF (2 drops) in CH2Cl2 (100 ml) at O° C., oxalyl chloride (1.0 gm, 8 mmol) was added in a drop-wise manner. After the addition, the reaction mixture was stirred at room temperature for 1 hour. Simultaneously, in a separate flask a mixture of hydroxylamine hydrochloride (2.0 gm, 29 mmol) and triethylamine (5 ml, excess) was stirred in THF:water (5:1, 30 ml) at O° C. for 1 hour. At the end of 1 hour, the oxalyl chloride reaction mixture was concentrated and the pale yellow residue was dissolved in 10 ml of CH2Cl2 and added slowly to the hydroxylamine at O° C. The reaction mixture was stirred at room temperature for 24 hours and concentrated. The residue obtained was extracted with chloroform and washed well with water. The product obtained was purified by silica gel column chromatography and eluted with ethyl acetate. The N-hydroxy-2-(4-methoxyphenylsulfanyl)-2-methyl-3-phenyl-propionamide was isolated as a colorless solid. mp 88° C.; Yield, 300 mg, 57%; MS: 318 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 1.32 (s, 3H), 3.07 (d, J=11 Hz, 1H), 3.23 (d, J=11 Hz, 1H), 3.79 (s, 3H), 6.83-7.36 (m, 9H).

Workup

  1. additionAfter the addition
  2. waitfor 1 hour
  3. concentrationwas concentrated
  4. dissolutionthe pale yellow residue was dissolved in 10 ml of CH2Cl2
  5. additionadded slowly to the hydroxylamine at O° C
  6. stirringThe reaction mixture was stirred at room temperature for 24 hours
  7. concentrationconcentrated
  8. customThe residue obtained
  9. extractionwas extracted with chloroform
  10. washwashed well with water
  11. customThe product obtained
  12. customwas purified by silica gel column chromatography
  13. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-b085f387882e41c99a7fa5a231d8ddc8
Source dataset
uspto-grants-2001_03
Patent number
US06197791B1

Reaction notes

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