Dimethyl Sulfoxide → HCID 10506910, compound

HRID 1456868Notes

Reaction equation

HRID 1456868 reaction equation
[CH3:1][C:2]([CH3:42])([CH:5]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=2)=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:8][CH:7]=1)[CH2:3][OH:4].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]([CH3:42])([CH:5]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=2)=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:8][CH:7]=1)[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22106652HCID 22106652, compound

Product 1

HCID 10506910HCID 10506910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a -78° C. solution in methylene chloride (15 mL) of 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propan-1-ol (0.4 g, 0.72 mmol), prepared as in step 1, and DMSO (0.17 g, 2.17 mmol) was added oxalyl chloride (0.14 g, 1.08 mmol) and the reaction mixture was stirred for 0.5 hours. Triethylamine (0.37 g, 3.6 mmol) was added via syringe, the ice bath was removed, and the reaction was allowed to warm to room temperature. The mixture was concentrated in vacuo and triturated with dry THF. The THF solution was filtered and washed with additional THF. The THF solution and washings were combined and concentrated in vacuo to give crude 2,2-dimethyl-3,3-bis(4-(2-quinolylmethoxy)phenyl)propanal which was used without further purification for oxime formation.

Workup

  1. customthe ice bath was removed
  2. concentrationThe mixture was concentrated in vacuo
  3. customtriturated with dry THF
  4. filtrationThe THF solution was filtered
  5. washwashed with additional THF
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9642b45fa48446348df939eebdee2059
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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