Calcium Carbonate → 2,2,2-Trifluoro-N-[2-(2-iodo-5-methoxyphenyl)ethyl]acetamide

HRID 967232ノート

反応式

HRID 967232 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][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:23]Cl>CO>[F:1][C:2]([F:16])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([O:14][CH3:15])[CH:11]=[CH:12][C:13]=1[I:23])=[O:4]

参加物

5

反応物 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 22292822HCID 22292822、化合物

生成物 1

HCID 222927722,2,2-Trifluoro-N-[2-(2-iodo-5-methoxyphenyl)ethyl]acetamide収率 99.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of N-trifluoroacetyl-3-methoxyphenethylamine (15.8 g, 64 mmol) in methanol (325 mL) was cooled to −78 C., and treated with CaCO3 (14.7 g, 145 mmol), followed by a solution of ICl (29 g, 181 mmol) in methanol (40 mL). The reaction was allowed to warm to 20 C. while stirring overnight and then 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 23.8 g of a white solid powder. 1H NMR (400 MHz, CDCl3) d 7.68 (d, J=9 Hz, 1 H), 6.76 (s, 1 H), 6.57 (d, J=9 Hz, 1 H), 6.42 (bs, 1 H), 3.77 (s, 3 H), 3.61 (dd, J=7, 7 Hz, 2 H), 2.99 (dd, J=7, 7 Hz, 2 H). MS calculated for C11H11F3INO2+H: 374, observed: 374.

後処理

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

出典と根拠

ORDレコード
ord-dd870ed84b584fb7b64467a403f625da
出典データセット
uspto-grants-2005_10
特許番号
US06953787B2

反応ノート

読み込み中…