(o-Carboxyphenylthio)acetic acid → (3-Chlorobenzo[b]thiophen-2-ylmethyl)methylamine

HRID 1711814

반응식

HRID 1711814 반응식
O=P(Cl)(Cl)[Cl:3].[C:6]([CH2:9][S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=O)(O)=O.[CH3:20][N+:21]([CH3:24])=[CH:22][Cl:23].[Cl-:25]>CN(C=O)C>[CH3:20][N+:21]([CH3:24])=[CH:22][Cl:23].[Cl-:3].[Cl:25][C:13]1[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10][C:9]=1[CH2:6][NH:21][CH3:20]

참가 물질

6

반응물 3

HCID 8660(o-Carboxyphenylthio)acetic acidHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chloride

생성물 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 6424818(3-Chlorobenzo[b]thiophen-2-ylmethyl)methylamine수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Vilsmeier reagent was prepared via the dropwise addition of POCl3 (7.9 mL, 84 mmol) into ice-cold DMF (14 mL). A solution of 2-carboxymethylsulfanyl-benzoic acid (3.0 g, 14 mmol) in DMF (15 mL) was added dropwise to the Vilsmeier reagent. The resulting mixture was warmed to room temperature and then heated to 80° C. for 3.5 h. The reaction mixture was cooled to ambient temperature. Crushed ice was added until a bright yellow precipitate appeared. The solid was isolated by filtration. Purification by flash column chromatography (silica gel, hexanes/ethyl acetate 3:2) gave the title compound (1.87 g, 68%) as a yellow powder: 1H NMR (300 MHz, CDCl3) δ 10.36 (s, 1H), 8.03 (m, 1H), 7.86 (m, 1H), 7.59-7.53 (m, 2H).

후처리

  1. temperatureheated to 80° C. for 3.5 h
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. additionCrushed ice was added until a bright yellow precipitate
  4. customThe solid was isolated by filtration
  5. customPurification by flash column chromatography (silica gel, hexanes/ethyl acetate 3:2)

출처 및 근거

ORD 기록
ord-b16528000504454a92d4b3c2da1572aa
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790709B2

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