Dimethylformamide → HCID 18381501, compound

HRID 2298090Notes

Reaction equation

HRID 2298090 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.C[N:14]([CH3:17])C=O.[C:18](Cl)(=O)[C:19](Cl)=O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][Br:12])=[CH:7][C:3]=1[C:4]([NH:14][CH2:17][C:19]12[CH2:18][CH:10]3[CH2:9][CH:8]([CH2:7][CH:3]([CH2:2]3)[CH2:4]1)[CH2:11]2)=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 18381494HCID 18381494, compound

Product 1

HCID 18381501HCID 18381501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-bromomethyl-benzoic acid (6.1 g) in dichloromethane (100 ml) at 0° C. were added dimethylformamide (0.2 ml) followed by oxalylchloride (3 ml). The reaction was stirred at room temperature for 0.5 hour and concentrated under vacuum. The acylchloride was redissolved in dichloromethane (100 ml) and and di-isopropylethylamine (6 ml) followed by adamantanemethylamine (3.5 ml) added at 0° C. The mixture was stirred at 0° C. for 10 min., then partitioned between diethyl ether and 1N aqueous hydrochloric acid. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude material was purified by recrystallisation from dichloromethane/ethylacetate/i-hexane to afford the title compound as a white solid (6.5 g) (sample contained some of the corresponding benzyl chloride).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe acylchloride was redissolved in dichloromethane (100 ml)
  3. additionadded at 0° C
  4. stirringThe mixture was stirred at 0° C. for 10 min.
  5. custompartitioned between diethyl ether and 1N aqueous hydrochloric acid
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by recrystallisation from dichloromethane/ethylacetate/i-hexane

Sources & evidence

ORD record
ord-839ca9ef321d43628a40d7151e34cb2e
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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