tert-Butyl mercaptan → 2-tert-Butylsulfanylmethyl-4-nitro-benzoic acid ethyl ester

HRID 390411노트

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HRID 390411 반응식
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH2:14]Br)[CH3:2].[CH3:17][C:18]([SH:21])([CH3:20])[CH3:19].[H-].[Na+]>CC#N>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH2:14][S:21][C:18]([CH3:20])([CH3:19])[CH3:17])[CH3:2]

참가 물질

5

반응물 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 58066683Ethyl 2-(bromomethyl)-4-nitrobenzoate

생성물 1

HCID 580666792-tert-Butylsulfanylmethyl-4-nitro-benzoic acid ethyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

2-Bromomethyl-4-nitro-benzoic acid ethyl ester (8.0 g, 27.8 mmol) and 2-methyl-2-propanethiol (3.74 mL, 33.3 mmol) were combined in MeCN (100 mL) at 0° C. Sodium hydride (60% in mineral oil; 1.39 g, 34.8 mmol) was added, and the reaction was stirred for 5 minutes at 0° C., and then at room temperature until no starting material was seen by analytical tlc. The mixture was quenched by adding ice chips and diluted with H2O (100 mL) and 1N aqueous HCl (30 mL), and then extracted with EtOAc. The combined organic layers were washed with H2O, dried, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

후처리

  1. customat room temperature
  2. customThe mixture was quenched
  3. additionby adding ice chips
  4. additiondiluted with H2O (100 mL) and 1N aqueous HCl (30 mL)
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with H2O
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-91d8d28dc8144ad793f8cc65f37778e0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383654B2

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