Oxalyl chloride → 7-Phenyl-3-phenylsulfanylheptanoic acid hydroxyamide

HRID 1107110Notes

Reaction equation

HRID 1107110 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C:13](O)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:31][NH2:32]>C(Cl)Cl>[OH:31][NH:32][C:13](=[O:14])[CH2:12][CH:11]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 18790157HCID 18790157, compound

Product 1

HCID 179155207-Phenyl-3-phenylsulfanylheptanoic acid hydroxyamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

7-Phenyl-3-phenylsulfanylheptanoic acid (2 g; 6.5 mmol) is dissolved in CH2Cl2 (20 mL) and cooled to 0° C. Oxalyl chloride (1.1 mL, 13 mmol) is added dropwise, the bath removed and the reaction allowed to warm and stir at 20° C. for 2 hours. The reaction is then concentrated in vacuo and azeotroped with CH2Cl2. The resulting oil is dissolved in CH2Cl2 (20 mL), cooled to 0° C. and O-(trimethylsilyl)hydroxylamine (1.7 g, 16 mmol) is added dropwise. The bath is removed and the reaction is allowed to warm to 20° C. The reaction is then partitioned between CH2Cl2 (100 mL) and 1 N HCl (50 mL), the organic layer is then separated and washed with water (40 mL), dried (MgSO4) and concentrated in vacuo to yield 7-phenyl-3-phenylsulfanylheptanoic acid hydroxyamide.

Workup

  1. customthe bath removed
  2. temperatureto warm
  3. concentrationThe reaction is then concentrated in vacuo
  4. customazeotroped with CH2Cl2
  5. dissolutionThe resulting oil is dissolved in CH2Cl2 (20 mL)
  6. temperaturecooled to 0° C.
  7. customThe bath is removed
  8. temperatureto warm to 20° C
  9. customThe reaction is then partitioned between CH2Cl2 (100 mL) and 1 N HCl (50 mL)
  10. customthe organic layer is then separated
  11. washwashed with water (40 mL)
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-979bbd332ca5411e86473c6d9b3f8f7c
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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