Methanol → HCID 22708819, compound

HRID 353345Notes

Reaction equation

HRID 353345 reaction equation
[CH2:1]([Cl:3])Cl.CO.[C:6]([O-:9])([O-])=O.[Ca+2].[I-:11].[Cl-].[Cl-].C[N+:15](C)(C)[CH2:16][C:17]1[CH:22]=C[CH:20]=[CH:19][CH:18]=1.C[N+](C)(C)CC1C=CC=CC=1.C[N+](C)(C)CC1C=CC=CC=1>O>[Cl:3][C:1]1[C:16]([NH2:15])=[C:17]([CH3:22])[C:18]([O:9][CH3:6])=[C:19]([I:11])[CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 10112Calcium CarbonateHCID 22708828HCID 22708828, compound

Product 1

HCID 22708819HCID 22708819, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of intermediate (22) (0.23 mol), DCM (200 ml), methanol (70 ml) and CaCO3 (0.3 mol) was stirred at room temperature. N,N,N-trimethylbenzenemethanaminium dichlorideiodide (0.23 mol) was added portionwise. The reaction mixture was stirred and refluxed for 2 hours. The mixture was cooled, then taken up into water. This mixture was extracted with DCM. The combined organic layers were washed with water, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2). The desired fractions were collected and the solvent was evaporated, yielding 33.9 g 6-chloro-4-iodo-3-methoxy-2-methylbenzenamine (49.3%) (interm. 23).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturerefluxed for 2 hours
  3. temperatureThe mixture was cooled
  4. extractionThis mixture was extracted with DCM
  5. washThe combined organic layers were washed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
  10. customThe desired fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-436edd6f64fe42388d87c566c6df8be6
Source dataset
uspto-grants-2004_06
Patent number
US06750349B2

Reaction notes

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