Diethylamine → 3-(Diethylsulfamoyl)benzoic acid

HRID 450636

反応式

HRID 450636 の反応式
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:9])=[O:8]>ClCCl>[CH2:1]([N:3]([CH2:4][CH3:5])[S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:9])=[O:8])[CH3:2]

参加物

4

反応物 2

HCID 8021DiethylamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

生成物 1

HCID 7945953-(Diethylsulfamoyl)benzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Diethylamine (Aldrich, 2.5 mL, 24 mmol) was added to a solution of 3-(chlorosulfonyl)benzoic acid (Aldrich, 2.0 g, 9.1 mmol) in anhydrous dichloromethane (20 mL) at 0° C. The mixture was then stirred at 0° C. for 2 hours. The volatiles were removed under reduced pressure. The residue was treated with aqueous potassium hydrogensulfate (1 M, 10 mL) and then extracted with ethyl acetate (3×50 mL). The combined extracts were dried over magnesium sulfate filtered and then concentrated to give the title compound. 1H NMR (300 MHz, CD3OD) δ 1.13 (t, J=7.1 Hz, 6 H), 3.22-3.30 (m, 4 H), 7.69 (t, J=7.8 Hz, 1H), 8.03 (ddd, J=7.9, 1.9, 1.4 Hz, 1 H), 8.25 (dt, J=7.8, 1.4 Hz, 1 H), 8.40 (t, J=1.7 Hz, 1 H) ppm; MS (DCI/NH3) m/z 275 (M+NH4)+.

後処理

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was treated with aqueous potassium hydrogensulfate (1 M, 10 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-11a040045ce842b58aebe0b96413b671
出典データセット
uspto-grants-2013_07
特許番号
US08486979B2

関連ノート

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