Toluene → 4-Iodo-N-methoxy-N-methyl-benzamide

HRID 534243Notes

Reaction equation

HRID 534243 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[I:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[I:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:3]([O:4][CH3:5])[CH3:2])=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 743734-Iodobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 54617564-Iodo-N-methoxy-N-methyl-benzamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N,O-Dimethylhydroxylamine hydrochloride (5.5 g, 56.4 mmol) was added to a suspension of 4-iodobenzoyl chloride (10.0 g, 37.5 mmol) and toluene (60 mL) at 0° C. After 10 min, a solution of sodium carbonate (16.0 g, 151 mmol) and water (250 mL) was added over 50 min via addition funnel. With vigorous stirring, the reaction was maintained at 0° C. for 2 h and then partitioned. The toluene layer was washed with water (125 mL), washed with brine (125 mL), and then concentrated. The residue was redissolved in toluene and filtered to remove trace solids. This solution was concentrated to give 10.5 g of 4-iodo-N-methoxy-N-methylbenzamide as a colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, 2H), 7.32 (d, 2H), 3.53 (s, 3H), 3.25 (s, 3H); LCMS: 292.4 (M+H)+. Step 2: 1-(4-Iodophenyl)-2-(4-methoxyphenyl)ethanone

Workup

  1. custompartitioned
  2. washThe toluene layer was washed with water (125 mL)
  3. washwashed with brine (125 mL)
  4. concentrationconcentrated
  5. dissolutionThe residue was redissolved in toluene
  6. filtrationfiltered
  7. customto remove trace solids
  8. concentrationThis solution was concentrated

Sources & evidence

ORD record
ord-e435a9921d42403884abef51020a067c
Source dataset
uspto-grants-2014_10
Patent number
US08853423B2

Reaction notes

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