Calcium Carbonate → N-trifluoroacetyl-1-(2-iodo-5-methoxyphenyl)-2-propylamine
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
Conditions
- Temperature
- 20 °C
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 bisulfite (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 C12H13F31NO2+H: 388, observed: 388.
Workup
- filtrationThe product mixture was filtered
- concentrationconcentrated
- dissolutiondissolved in EtOAc (200 mL)
- washwashed twice with 5% aqueous sodium bisulfite (100 mL), once with brine (100 mL)
- dry with materialdried with Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8c29ecd2f8df45af8327e3ec7a6cf980
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153621B2
Reaction notes
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