Dimethyl Sulfoxide → HCID 14484906, compound

HRID 1089612Notes

Reaction equation

HRID 1089612 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:25][CH2:26][CH2:27][C:28]1[C:36]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:35][C:31]2[CH2:32][CH2:33][O:34][C:30]=2[CH:29]=1.CS(C)=O>O1CCCC1.O>[C:2]1([NH:1][CH2:25][CH2:26][CH2:27][C:28]2[C:36]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:35][C:31]3[CH2:32][CH2:33][O:34][C:30]=3[CH:29]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6115AnilineHCID 86744323HCID 86744323, compoundHCID 178418339Butyllithium

Product 1

HCID 14484906HCID 14484906, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a -78° solution of lithium anilide, prepared from aniline (0.217 g, 2.33 mmol) and n-butyllithium (1.6 M in hexane, 1.46 mL, 2.33 mmol), in tetrahydrofuran (2 mL) was added a solution of 8a (0.980 g, 2.23 mmol). Dimethyl sulfoxide (0.1 mL) was added and the mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ether (2 X). The extracts were dried (MgSO4) and concentrated to afford 12.

Workup

  1. extractionextracted with ether (2 X)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fe710324a2de4a88b724625d20c7252c
Source dataset
uspto-grants-1990_10
Patent number
US04966907

Reaction notes

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