Sulfuric Acid → HCID 22270723, compound

HRID 488592Notes

Reaction equation

HRID 488592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:9]([CH3:12])(O)[CH3:10])=[CH:4][CH:3]=1.[Cl:21][CH2:22][C:23]#[N:24].S(=O)(=O)(O)[OH:26]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:9]([NH:24][C:23](=[O:26])[CH2:22][Cl:21])([CH3:12])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 22270422HCID 22270422, compound

Product 1

HCID 22270723HCID 22270723, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 3,4-bis(4-chlorophenyl)-2-methyl-2-butanol (Step B, 1.4 g, 4.5 mmol) and chloroacetonitrile (0.57 mL, 9.1 mmol) in acetic acid (0.7 mL) at −10° C. was added concentrated sulfuric acid (0.31 mL, 14 mmol). After stirring at −10° C. for 15 min and room temperature for 2 h, the reaction mixture was poured onto ice (20 g), and the product was extracted with EtOAc (3×20 mL). The combined extracts were washed with brine/saturated aqueous sodium bicarbonate, dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the title compound.

Workup

  1. additionthe reaction mixture was poured onto ice (20 g)
  2. extractionthe product was extracted with EtOAc (3×20 mL)
  3. washThe combined extracts were washed with brine/saturated aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ce5cda038d3b4c3cb5fe053ac361b4c5
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

Loading…