Dimethylformamide → 3-chloro-N,N-diisopropyl-5-methoxy-benzamide

HRID 433958Notes

Reaction equation

HRID 433958 reaction equation
C(Cl)(=O)C([Cl:4])=O.CN([CH:10]=[O:11])C.[CH:12]([NH:15][CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13].CCN([CH:25]([CH3:27])[CH3:26])C(C)C.[O:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[Cl:4][C:32]1[CH:31]=[C:30]([CH:27]=[C:25]([O:11][CH3:10])[CH:26]=1)[C:29]([N:15]([CH:16]([CH3:18])[CH3:17])[CH:12]([CH3:14])[CH3:13])=[O:28]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 121143193-chloro-N,N-diisopropyl-5-methoxy-benzamide

Procedure

Oxalyl chloride (2.36 ml) was added dropwise to a solution of DMF (0.1 ml) and 3-chloro-5-methoxybenzoic acid3 (4.67 g) in anhydrous tetrahydrofuran (100 ml). After 1 h, diisopropylamine (3.75 ml) and DIPEA (9.51 ml) were added and stirring was continued for 18 h. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer extracted with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate and water. After drying the organic phase with brine and over sodium sulphate, the solvent was removed under reduced pressure to give the title compound as a brown solid (4.6 g).

Workup

  1. waitwas continued for 18 h
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionthe organic layer extracted with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate and water
  4. dry with materialAfter drying the organic phase with brine
  5. customover sodium sulphate, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b61ac93e4a594cd19b63e225955747af
Source dataset
uspto-grants-2003_12
Patent number
US06670381B2

Reaction notes

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