Triethylamine → N-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)ethyl]methanesulfonamide

HRID 1059651노트

반응식

HRID 1059651 반응식
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1COCC1>[O:14]=[C:6]1[N:5]([CH2:4][CH2:3][NH:2][S:23]([CH3:22])(=[O:25])=[O:24])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 186308891-(2-aminoethyl)-2,3-dihydro-1H-1,3-benzodiazol-2-one hydrochloride

생성물 1

HCID 18630866N-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)ethyl]methanesulfonamide수율 15.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(2-aminoethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (2.8 g, 13 mmoles) in THF (30 ml) and triethyl amine (5.5 ml, 39 mmoles) was added methanesulfonyl chloride (1.12 ml, 14 mmoles) and the reaction mixture was stirred for 2 hours at room temperature. The organic solvent was evaporated and the residue was partitioned into water and ethyl acetate. The organic layer was washed with saturated aqueous Na2CO3 solution and taken to dryness. The crude residue was purified by flash chromatography (CH2Cl2-methanol 96-4) to give 0.5 g of the title compound as a white solid. M.p. 162-170° C.

후처리

  1. customThe organic solvent was evaporated
  2. customthe residue was partitioned into water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous Na2CO3 solution
  4. customThe crude residue was purified by flash chromatography (CH2Cl2-methanol 96-4)

출처 및 근거

ORD 기록
ord-8d358ff621344339aee6be9fe820a88f
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521623B1

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