4-Methylmorpholine → benzenesulfonyl-acetic acid N'-[2-(4-iodo-phenyl)-acetyl]-hydrazide

HRID 602801ノート

反応式

HRID 602801 の反応式
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:15]C(C1C=CC=CC=1)C(O)=O.ON1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.CN1CC[O:40][CH2:39][CH2:38]1.CCN=C=NCCCN(C)C.[NH4+].[Cl-]>C1COCC1>[I:15][C:30]1[CH:35]=[CH:34][C:33]([CH2:38][C:39]([NH:14][NH:13][C:11](=[O:12])[CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])=[O:40])=[CH:32][CH:31]=1

参加物

8

反応物 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 9943159Iodophenylacetic acidHCID 11378890Benzenesulfonyl-acetic acid hydrazide

生成物 1

HCID 67266905benzenesulfonyl-acetic acid N'-[2-(4-iodo-phenyl)-acetyl]-hydrazide収率 469.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 1 g (4.7 mmol) of benzenesulfonyl-acetic acid hydrazide (example 74.1) in 4 mL of THF was treated with 391 mg (4.7 mmol) of iodophenylacetic acid, 126 mg (0.93 mmol) of 1-hydroxybenzotriazole and 2.8 g (28 mmol) of N-methylmorpholine. The mixture was stirred during 15 min at 0° C., treated with 1.25 g (6.5 mmol) of EDCI and stirred during 12 hrs. The crude was treated with diluted aqueous NH4Cl and extracted twice with EtOAc. Drying of the combined organic layers over Na2SO4, filtration and evaporation gave 2 g (93%) of benzenesulfonyl-acetic acid N′-[2-(4-iodo-phenyl)-acetyl]-hydrazide as a brown oil, MS: 266 (MH+)

後処理

  1. stirringstirred during 12 hrs
  2. extractionextracted twice with EtOAc
  3. dry with materialDrying of the combined organic layers over Na2SO4, filtration and evaporation

出典と根拠

ORDレコード
ord-184aee9abcfc4afcbfcf236f9652ebda
出典データセット
uspto-grants-2011_03
特許番号
US07906546B2

反応ノート

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