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

HRID 1059651ノート

反応式

HRID 1059651 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8d358ff621344339aee6be9fe820a88f
出典データセット
uspto-grants-2003_02
特許番号
US06521623B1

反応ノート

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