Dimethylamine → 2,3-difluoro-5-iodo-N,N-dimethyl-benzamide

HRID 2234683Notes

Reaction equation

HRID 2234683 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:13]([N:16](C(C)C)[CH2:17]C)(C)C.CC(C)(C)C(Cl)=O.CNC>ClCCl>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([N:16]([CH3:17])[CH3:13])=[O:5]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 108913672,3-Difluoro-5-iodobenzoic acid

Product 1

HCID 579757722,3-difluoro-5-iodo-N,N-dimethyl-benzamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Difluoro-5-iodo-benzoic acid (7.20 g, 25.35 mmol), di-iso-propylethylamine (4.5 ml, 25.83 mmol), trimethylacetyl chloride (3.2 ml, 25.98 mmol), and dichloromethane (100 ml) were combined and stirred at room temperature for 1 hour. Dimethylamine (2 M in tetrahydrofuran, 22.0 ml, 44.00 mmol) was added to the reaction, and the combined mixture was stirred for an addition 18 hours at room temperature. The mixture was concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel (0 to 40% ethyl acetate in hexanes) to afford 7.17 g (91%) of 2,3-difluoro-5-iodo-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, d6-DMSO) δ 8.02-7.90 (m, 1H), 7.60-7.54 (m, 1H), 2.99 (s, 3H), 2.84 (s, 3H); LCMS m/z 400.0 (M+H+); MS: m/z 312.0 (M+H+).

Workup

  1. stirringthe combined mixture was stirred for an addition 18 hours at room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe crude product was purified by flash chromatography on silica gel (0 to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b09cc885f3ba4b4cb59f9d6147e6fc13
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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