Dimethylamine → 3-(Dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride

HRID 59730노트

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HRID 59730 반응식
[Cl:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11])(=[O:4])=[O:3].C(Cl)(C(Cl)=O)=O.[CH3:22][NH:23][CH3:24].C1COCC1>C(Cl)Cl.CN(C=O)C>[CH3:22][N:23]([CH3:24])[C:10]([C:9]1[CH:13]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:6]=[CH:7][C:8]=1[O:14][CH3:15])=[O:11]

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 1040075-Chlorosulphonyl-2-anisic acid

생성물 1

HCID 457912293-(Dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a suspension of 5-(chlorosulfonyl)-2-methoxybenzoic acid (1.243 g, 4.96 mmol) in dry DCM (20 ml) cooled to 0° C., (COCl)2 (1.302 ml, 14.88 mmol) was added drop-wise followed by few drops of dry DMF and the reaction was stirred at RT for 1 hour. The mixture was concentrated under reduced pressure, treated with dry toluene (30 ml×2) and evaporated to dryness. The residue was suspended in dry toluene (20 ml) and the resulting suspension was cooled to 0° C.; a solution of dimethylamine 2.0 M in THF (4.96 ml, 9.92 mmol) was added drop-wise and the reaction was stirred at RT overnight. The mixture was diluted with DCM and washed with brine; the organic phase was dried over sodium sulfate and the solvent was removed. The crude was purified by flash chromatography on silica gel (EtOAc/petroleum ether=60/40) to give 3-(dimethylcarbamoyl)-4-methoxybenzene-1-sulfonyl chloride (Int. 9) (400 mg, 1.440 mmol, MS/ESI+278.0 [MH]+).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiontreated with dry toluene (30 ml×2)
  3. customevaporated to dryness
  4. temperaturethe resulting suspension was cooled to 0° C.
  5. stirringthe reaction was stirred at RT overnight
  6. washwashed with brine
  7. dry with materialthe organic phase was dried over sodium sulfate
  8. customthe solvent was removed
  9. customThe crude was purified by flash chromatography on silica gel (EtOAc/petroleum ether=60/40)

출처 및 근거

ORD 기록
ord-68e1d92529454547bff51fd4edd15e9e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

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