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

HRID 967232노트

반응식

HRID 967232 반응식
[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]

참가 물질

5

반응물 3

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 22292822HCID 22292822, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dd870ed84b584fb7b64467a403f625da
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953787B2

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