Hydrochloric Acid → 2-(4-Acetylbenzenesulfonamido)acetic acid

HRID 347343

반응식

HRID 347343 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH2:14][CH2:15][C:16]([OH:18])=[O:17].Cl>CC(C)=O.[OH-].[Na+].O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2664184-Acetylbenzenesulfonyl chloride

생성물 1

HCID 21201292-(4-Acetylbenzenesulfonamido)acetic acid수율 94%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

Ex-26A: To a solution of 4-acetylbenzenesulfonyl chloride (0.50 g, 2.3 mmol) in acetone (7.5 mL) was added a solution of glycine (0.42 g, 5.7 mmol) in 5% aqueous sodium hydroxide (2.5 mL) and the reaction was stirred for 30 min at room temperature. The mixture was diluted with water (10 mL), acidified with a 1 N hydrochloric acid solution, and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (2×20 mL), dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting solid was dried in vacuo to afford 0.55 g (94%) of (4-acetylbenzenesulfonylamino)acetic acid as a white solid, mp 213–215° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.28 (t, 1H, J=5.4 Hz), 8.12 (d, 2H, J=8.4 Hz), 7.92 (d, 2H, J=8.4 Hz), 3.64 (d, 2H, J=5.1 Hz), 2.64 (s, 3H). Anal. Calcd. for C10H11NO5S: C, 46.69; H, 4.31; N, 5.44; S, 12.46; Found: C, 46.76; H, 4.43; N, 5.39; S, 12.16.

후처리

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washThe combined organic layers were washed with brine (2×20 mL)
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting solid was dried in vacuo

출처 및 근거

ORD 기록
ord-70e74d112109419aa05a8de43b0508bc
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173129B2

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