Dimethylformamide → HCID 86640813, compound

HRID 2070867Notes

Reaction equation

HRID 2070867 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](NC)=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].CN(C)C=O.IC1C=CC(C(O)=O)=CC=1OC.S(Cl)([Cl:34])(=O)=O>>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([Cl:34])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24648Sulfuryl chlorideHCID 179342274-Iodo-3-methoxybenzoic acidHCID 59276645HCID 59276645, compound

Product 1

HCID 86640813HCID 86640813, compound

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. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe excess sulfuryl dichloride was removed under reduced pressure

Sources & evidence

ORD record
ord-100c544fc9ef4197b7651b566e6a1bc4
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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