Methanol → HCID 18426776, compound

HRID 1281104Notes

Reaction equation

HRID 1281104 reaction equation
C(Cl)Cl.[CH3:4][OH:5].C([O-])([O-])=O.[Ca+2].[I-:11].[Cl-:12].[Cl-].C[N+:15](C)(C)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:25][N+](C)(C)CC1C=CC=CC=1.C[N+](C)(C)CC1C=CC=CC=1>O>[Cl:12][C:18]1[C:17]([CH2:16][NH2:15])=[C:22]([CH3:21])[C:4]([O:5][CH3:25])=[C:20]([I:11])[CH:19]=1

Participants

6

Reactant 4

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

Product 1

HCID 18426776HCID 18426776, 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-trimethylbenzene-methanaminium 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-methylbenzylamine (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-a937b92af3a44421b27267f50ffb7568
Source dataset
uspto-grants-2002_09
Patent number
US06452013B1

Reaction notes

Loading…