HCID 12976796, compound → HCID 10081144, compound

HRID 1485637Notes

Reaction equation

HRID 1485637 reaction equation
[C-]1C2C(=CC3C(C=2)=CC=CC=3)C=CC=1.[Na+].[CH3:16][S:17](=[N:24]S(C1C=CC(C)=CC=1)(=O)=O)([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18]>COCCOC>[NH:24]=[S:17]([CH3:16])([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18]

Participants

4

Reactant 2

HCID 12976796HCID 12976796, compoundHCID 122496144HCID 122496144, compound

Product 1

HCID 10081144HCID 10081144, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of sodium anthracenide (0.6 M in 1,2-dimethoxyethane; 20 mL) is added drop wise to methyl[(4-methylbenzenesulfonyl)imino]pyrrolidin-1-yl-λ6-sulfanone (2.00 g) in 1,2-dimethoxyethane (10 mL) at 0° C. until the blue color persists for a few minutes. The reaction mixture is quenched with hydrochloric acid (3 N; 3 mL), diluted with dichloromethane (60 mL), and stirred for a few minutes. The aqueous phase is separated, washed with dichloromethane and diethyl ether, and basified with solid sodium carbonate. The water is removed in vacuo and the dry residue is stirred with dichloromethane (20 mL) for 1 h. The extract is filtered, dried over MgSO4, and concentrated in vacuo to give the title compound. Mass spectrum (ESI+): m/z=149 [M+H]+.

Workup

  1. customThe reaction mixture is quenched with hydrochloric acid (3 N; 3 mL)
  2. additiondiluted with dichloromethane (60 mL)
  3. customThe aqueous phase is separated
  4. washwashed with dichloromethane and diethyl ether
  5. customThe water is removed in vacuo
  6. stirringthe dry residue is stirred with dichloromethane (20 mL) for 1 h
  7. filtrationThe extract is filtered
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49f853f9831846a6a93ea746ac908a19
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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