Dimethylformamide → HCID 69410881, compound

HRID 1350332Notes

Reaction equation

HRID 1350332 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][C:4]=1[C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1CCl.[CH3:30][N:31]([CH3:34])C=O>>[N:31]1[CH:34]=[CH:5][C:4]([CH:12]([O:10][C:9](=[O:11])[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:12]([OH:14])=[O:13])[CH:5]=2)[C:25]2[CH:24]=[CH:23][N:22]=[CH:27][CH:26]=2)=[CH:3][CH:30]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 751524-Methoxyisophthalic acid

Product 1

HCID 69410881HCID 69410881, compoundYield 48%

Procedure

In N,N-dimethylformamide (“DMF”) (25 mL) was stirred 4-methoxy-1,3-benzenedicarboxylic acid (675 mg, 3.4 mmol) and potassium carbonate (4.3 g, 31 mmol). To this was added in parts, picolyl chloride hydrochloride (1.23 g, 7.5 mmol). The mixture was stirred at room temperature 24 hours. The mixture was filtered free of insoluble material and the DMF solution evaporated at reduced pressure to give a solid. This was partitioned between methylene chloride (100 mL) and saturated sodium bicarbonate solution (100 mL). The organic phase was separated and washed with water (100 mL) and then brine (100 mL). The organic phase was dried over magnesium sulfate and evaporated at reduced pressure to give 0.619 g (48%) of a tan solid. MS: M+1=379.1.

Workup

  1. filtrationThe mixture was filtered free of insoluble material
  2. customthe DMF solution evaporated at reduced pressure
  3. customto give a solid
  4. customThis was partitioned between methylene chloride (100 mL) and saturated sodium bicarbonate solution (100 mL)
  5. customThe organic phase was separated
  6. washwashed with water (100 mL)
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-4f3157e3742a4b49a456d53112eb526b
Source dataset
uspto-grants-2007_05
Patent number
US07214712B2

Reaction notes

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