Hydrochloric Acid → Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

HRID 1428713ノート

反応式

HRID 1428713 の反応式
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>CN(C)C=O.FC(F)(F)C(O)=O.[Mn]>[CH3:11][S:8]([NH:7][CH2:6][C:5]1[CH:12]=[CH:13][C:2]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 10807Ethyl 2-chloropropionateHCID 19027423N-[(4-bromophenyl)methyl]methanesulfonamide

生成物 1

HCID 70816013Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

試薬・触媒・溶媒 3

HCID 6422Trifluoroacetic acid触媒HCID 23930Manganese触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of N-(4-bromobenzyl)methanesulfonamide (675 mg, 2.555 mmol) in dimethylformamide were added ethyl 2-chloropropionate (0.42 mL), manganese (280 mg) and (2,2′-bipyridine)nickel(II)-dibromide (67 mg, 0.17885 mmol). Trifluoroacetic acid (2 drops) was added. The reaction mixture was stirred for 36 h at 60° C. After cooling down to room temperature, the mixture was hydrolysed by 1N HCl and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to obtain ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 mg).

後処理

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-416544318e194d2bb5f564fc25217aea
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

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