Calcium Carbonate → N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine

HRID 2389436Notes

Reaction equation

HRID 2389436 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH:6]([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:4].C([O-])([O-])=O.[Ca+2].[I:24]Cl>CO>[F:1][C:2]([F:17])([F:18])[C:3]([NH:5][CH:6]([CH3:16])[CH2:7][C:8]1[CH:9]=[C:10]([O:14][CH3:15])[CH:11]=[CH:12][C:13]=1[I:24])=[O:4]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 14964390N-(Trifluoroacetyl)-1-(3-methyloxyphenyl)propan-2-ylamine

Product 1

HCID 86590367N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamineYield 110.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N-trifluoroacetyl-1-(3-methoxyphenyl)-2-propylamine (4.29 g, 15.7 mmol) in methanol (100 mL) was cooled to −78 C. and treated with CaCO3 (3.17 g, 31.4 mmol), followed by a solution of ICl (6.37 g, 39.3 mmol) in methanol (50 mL). The reaction was allowed to warm to 20 C. while stirring overnight. The product mixture was filtered, concentrated, dissolved in EtOAc (200 mL), washed twice with 5% aqueous sodium bisulfate (100 mL), once with brine (100 mL), dried with Na2SO4 and concentrated to give 6.72 g of a white solid powder. MS calculated for C12H13F3INO2+H: 388, observed: 388.

Workup

  1. temperatureto warm to 20 C
  2. filtrationThe product mixture was filtered
  3. concentrationconcentrated
  4. dissolutiondissolved in EtOAc (200 mL)
  5. washwashed twice with 5% aqueous sodium bisulfate (100 mL), once with brine (100 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2581fc4b717b48bab1e8debb62be7426
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

Loading…