Thionyl Chloride → HCID 67233406, compound

HRID 1465936Notes

Reaction equation

HRID 1465936 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:11](CC2C=CC(OC)=CC=2OC)[CH2:10][C:9]2[CH:23]=[C:24]([Br:26])[S:25][C:8]=2[C:7]1=[O:27])=[O:5])[CH3:2].S(Cl)(Cl)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[CH:23]=[C:24]([Br:26])[S:25][C:8]=2[C:7]=1[OH:27])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67235046HCID 67235046, compound

Product 1

HCID 67233406HCID 67233406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-5-(2,4-dimethoxy-benzyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester (example 21.c, 5.66 g, 12.5 mmol) was dissolved in 85 mL of anhydrous dichloromethane. To the solution was added 1.37 mL of thionyl chloride, and the reaction mixture was stirred for 5 hours. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to 3.1 g of off-white solid: MS: (+) m/z 300.0, 301.9 (M+1, 79Br/81Br)

Workup

  1. filtrationThe solution was filtered on a fine glass frit
  2. filtrationfilter
  3. customto collect a white solid precipitate
  4. washThe solid was washed twice with cold dichloromethane
  5. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  6. washThe organic fraction was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to 3.1 g of off-white solid

Sources & evidence

ORD record
ord-6a20f05c252547c2908b13663b3cde2e
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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