Tributylphosphine → HCID 66764153、化合物

HRID 921999

反応式

HRID 921999 の反応式
[Cl:1][CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:4].[CH2:16]([P:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>C(OCC)(=O)C>[Cl-:1].[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][C:3](=[O:4])[CH2:2][P+:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

参加物

4

反応物 2

HCID 13831TributylphosphineHCID 132776644-Acetamidophenyl chloroacetate

生成物 1

HCID 66764153HCID 66764153、化合物収率 65%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

4-Acetamidophenyl 2-chloroacetate [2] (1.138 g, 5 mmol) and tributylphosphine (0.475 g, 6 mmol) were suspended in 50 ml of anhydrous ethyl acetate and refluxed for 48 hrs. After cooling to room temperature the white precipitate was filtered, washed with ethylacetate and diethylether and dried under reduced pressure to give [6]. The crude product was crystallized twice from acetonitrile to give pure [6] in 65% yield. Identity and purity was confirmed via 1H and 13C NMR. The desired compound is isolated as colourless needles. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=10.49 (s, 1H), 7.71 (d, J=8.95 Hz, 2H), 7.12 (d, J=8.95 Hz, 2H), 4.18 (d, J=14.33, 2H), 2.41 (m, 3H), 2.06 (s, 3H), 1.55 (m, 6H), 1.41 (m, 6H), 0.91 (t, J=7.17). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=34.8. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=168.4, 164.7, 144.8, 137.8, 121.4, 119.9, 25.8 (d, J=47.9 Hz), 23.9, 23.3 (d, J=16.77 Hz), 22.6 (d, J=4.43 Hz), 18.2 (d, J=47.7 Hz), 13.2. mp 199° C. (dec), T5%onset 197° C.

後処理

  1. temperaturerefluxed for 48 hrs
  2. filtrationwas filtered
  3. washwashed with ethylacetate and diethylether
  4. customdried under reduced pressure

出典と根拠

ORDレコード
ord-3b86c66b24b64d1b8e6328e38ca4601f
出典データセット
uspto-grants-2016_03
特許番号
US09278134B2

関連ノート

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