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Hydroxylamine → 2-{[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)amino}-N-hydroxy-acetamide

HRID 1662973
ノート
印刷プレビュー

反応式

HRID 1662973 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH2:25][C:26]([OH:28])=O)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[NH2:40][OH:41].N#N>C(Cl)Cl.O.C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:25][C:26]([NH:40][OH:41])=[O:28])(=[O:14])=[O:13])=[CH:8][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 787HydroxylamineHCID 947NitrogenHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 21884785{[4-(3-Chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid

生成物 1

HCID 99330622-{[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)amino}-N-hydroxy-acetamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

To a solution of 48.81 g (0.114 mol) of {[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxybenzyl)-amino}-acetic acid in 500 ml of CH2Cl2, 19.56 ml (0.228 mol) of oxalyl chloride and 0.88 ml (0.011 mol) of DMF are added dropwise at 0-5° C. under N2 atmosphere. The mixture is stirred for 1 h at 0-5° C. and 1 h at r.t. To a solution of 226 ml (3.42 mol) of) 50% hydroxylamine in H2O (Aldrich) in 1200 ml of THF, a solution of the freshly prepared above acid chloride in CH2Cl2 is added over 45 min. at −10 to −5° C. through a teflon tube using N2 gas pressure. The reaction mixture is stirred for 30 min at −5 to 0° C. and filtered through, paper filter to remove insoluble precipitates. The filtrate is diluted with H2O and extracted with CH2Cl2. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The product is collected by filtration and washed with ether to give 43.03 g of 2-{[4-(3-chloro-propoxy)-benzenesulfonyl]-(4-methoxy-benzyl)amino}-N-hydroxy-acetamide; NMR (CDCl3): 2.2-2.35 (m, 2H), 3.69 (s, 2H), 3.76 (t, 2H, J=6 Hz), 3.79 (s, 3H), 4.21 (t, 2H, J=6 Hz), 4.26 (s, 2H), 6.77 (br s, 1H), 6.85 (d, 2H, J=9.04 Hz), 7.03 (d, 2H, J=9.04 Hz), 7.15 (d, 2H, J=9.04 Hz), 7.78 (d, 2H, J=8.56 Hz), 8.82 (br s, 1H).

後処理

  1. additionis added over 45 min. at −10 to −5° C. through a teflon tube
  2. stirringThe reaction mixture is stirred for 30 min at −5 to 0° C.
  3. filtrationfiltered through, paper
  4. filtrationfilter
  5. customto remove insoluble precipitates
  6. additionThe filtrate is diluted with H2O
  7. extractionextracted with CH2Cl2
  8. washThe combined extracts are washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. filtrationThe product is collected by filtration
  12. washwashed with ether

出典と根拠

ORDレコード
ord-486821c0bd084ccb9d7b806c22c4d789
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08034810B2

反応ノート

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