Water → HCID 59276645, compound

HRID 2070868Notes

Reaction equation

HRID 2070868 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[I:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][C:12]=1[O:20][CH3:21].O>ClCCl>[I:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:5][CH3:3])=[O:16])=[CH:13][C:12]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8471TriethylamineHCID 86640813HCID 86640813, compound

Product 1

HCID 59276645HCID 59276645, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Iodo-3-methoxy-N-methylbenzamide. N,N-Dimethylformamide (0.1 mL) was added to a solution of 4-iodo-3-methoxybenzoic acid (2.0 g, 7.2 mmol) in sulfuryl dichloride (20 mL), and the mixture was heated to reflux for 2 h. The excess sulfuryl dichloride was removed under reduced pressure to give the crude product 4-iodo-3-methoxy-benzoyl chloride. To a solution of methyl amine (0.72 g, 10.8 mmol) and triethylamine (2.18 g, 21.6 mmol) in dichloromethane (20 mL) was added dropwise a solution of the above 4-iodo-3-methoxy-benzoyl chloride in dichloromethane (15 mL) at 0° C. After the reaction was completed, water was added, the organic layer was separated, dried over sodium sulfate evaporated to give the crude product, which was purified on silica gel column (eluting with 10-17% ethyl acetate in petroleum ether) to give 4-iodo-3-methoxy-N-methylbenzamide (0.92 g, 46% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.92 (d, J=8.0 Hz, 1H), 7.42 (d, J=5.6 Hz, 1H), 7.31 (dd, J1=8.0 Hz, J2=2.0 Hz, 1H), 3.88 (s, 3H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customto give the crude product, which
  5. customwas purified on silica gel column (eluting with 10-17% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a3b7d09b91b84a13a7ff3428d6595184
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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