4-Aminobenzonitrile → HCID 2812223、化合物

HRID 2272584ノート

反応式

HRID 2272584 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[S:10]([CH2:15][C:16](O)=[O:17])[CH2:11][C:12]([OH:14])=[O:13].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C1COCC1.O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:16](=[O:17])[CH2:15][S:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:3][CH:4]=1)#[N:7]

参加物

8

反応物 4

HCID 133964-AminobenzonitrileHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31277Thiodiglycolic acidHCID 81531Diisopropylethylamine

生成物 1

HCID 2812223HCID 2812223、化合物収率 15.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-aminobenzonitrile (500 mg, 4.23 mmol), 2,2′-thiodiacetic acid (3.18 g, 21.2 mmol), WSC (4.87 g, 25.4 mmol), DMAP (258 mg, 0.21 mmol) and DIEA (5.47 g, 42.3 mmol) in THF (200 mL) was stirred at room temperature for 60 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give 2-((2-((4-cyanophenyl)amino)-2-oxoethyl)thio)acetic acid (162 mg, 15.3%) as a pale-yellow powder.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-65d63c0180f04085ab062edf85987af1
出典データセット
uspto-grants-2015_09
特許番号
US09120776B2

反応ノート

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