5-Bromo-2-methyl-1H-benzo[d]imidazole → HCID 58107460, 화합물

HRID 1810192노트

반응식

HRID 1810192 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[NH:7][C:6]=2[CH:11]=1.C([Li])(C)(C)C.[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([C:22](N(OC)C)=[O:23])=[CH:20][C:19]=1[S:30](=[O:33])(=[O:32])[NH2:31]>O1CCCC1>[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([C:22]([C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[C:8]([CH3:10])[NH:7][C:6]=3[CH:11]=2)=[O:23])=[CH:20][C:19]=1[S:30]([NH2:31])(=[O:33])=[O:32]

참가 물질

5

반응물 3

HCID 6109795-Bromo-2-methyl-1H-benzo[d]imidazoleHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 58107460HCID 58107460, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 0.303 g of 6-bromo-2-methyl-1H-benzoimidazole in tetrahydrofuran (20 mL) is cooled to −50° C. and treated with 2.7 mL of tert-butyllithium (1.5 M in pentane). After 2 h at −50° C. the reaction mixture is treated with 0.12 g of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide in tetrahydrofuran (10 mL). After 3 h the mixture is quenched with saturated aqueous ammonium chloride, taken up in ethyl acetate, and washed with saturated aqueous sodium chloride. The organics are dried (magnesium sulfate), concentrated and purified by silica gel chromatography (98:2 methylene chloride/methanol) to give 2-chloro-5-(2-methyl-3H-benzoimidazole-5-carbonyl)-benzenesulfonamide. MS (m/z): 348 (M−1); Rf 0.30 (9:1 methylene chloride/methanol).

후처리

  1. customAfter 3 h the mixture is quenched with saturated aqueous ammonium chloride
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialThe organics are dried (magnesium sulfate)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (98:2 methylene chloride/methanol)

출처 및 근거

ORD 기록
ord-73cba3e20b064e1fa3fc5603d7855bbf
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362063B2

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