Water → HCID 13125989, 화합물

HRID 1389811노트

반응식

HRID 1389811 반응식
O[CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:5]=2[N:4]([CH2:20][CH3:21])[C:3]1=[O:22].C(N(S(F)(F)[F:29])CC)C.O>C(Cl)Cl>[F:29][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:5]=2[N:4]([CH2:20][CH3:21])[C:3]1=[O:22]

참가 물질

5

반응물 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 1312600662659-64-7

생성물 1

HCID 13125989HCID 13125989, 화합물수율 57.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3.5 g (0.01 mol) of 3-hydroxy-1,3-dihydro-1-ethyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one in 7 ml of anhydrous methylene chloride was added dropwise to a stirred solution of 3.53 ml (0.028 mol) of diethylaminosulfur trifluoride in 84 ml of anhydrous methylene chloride cooled to -70°. The reaction mixture was allowed to warm slowly to 5° and then poured into 150 ml of ice and water. The lower organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to give 2.84 g (90% yield) of crude product as light yellow crystals. Recrystallization from 200 ml of heptane gave 1.81 g (57% yield) of 3-fluoro-1,3-dihydro-1-ethyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one: mp 156°-158°; 1H nmr (DMSO-d6) δ 7.2-7.8 ppm (m, 8H), δ 5.85 ppm (d, 1H, J=57 Hz), δ 3.5-4.38 (m, 2H, methylene protons on nitrogen), δ 1.02 (t, 3H).

후처리

  1. temperaturecooled to -70°
  2. temperatureto warm slowly to 5°
  3. customThe lower organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customto give 2.84 g (90% yield) of crude product as light yellow crystals
  8. customRecrystallization from 200 ml of heptane

출처 및 근거

ORD 기록
ord-be43b780b06048338ddefb4ea9fd7dd3
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04246270

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