Hydrochloric Acid → Methyl 4-[(2-propynylamino)carbonyl]benzoate

HRID 1722422노트

반응식

HRID 1722422 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.S(Cl)(Cl)=O.Cl.[N:19]1C=C[CH:22]=[CH:21][CH:20]=1>N#N.CCCCCC.C(O)(=O)C>[CH2:20]([NH:19][C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:12][CH:11]=1)=[O:10])[C:21]#[CH:22]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2회HCID 15513Monomethyl terephthalateHCID 24386Thionyl Chloride

생성물 1

HCID 14180955Methyl 4-[(2-propynylamino)carbonyl]benzoate

시약·촉매·용매 2

HCID 947Nitrogen용매HCID 22590778Acetic Acid Hexane용매

실험 절차

Terephthalic acid mono methyl ester (0.775 g) was dissolved in dry pyridine (10 ml) in a N2 atmosphere. The solution was cooled in an ice-water bath, and thionyl chloride (0.44 ml) was added dropwise. The mixture was warmed to room temperature and was stirred for 1 h to give a pale brown suspension. The mixture was re-cooled in an ice-water bath, and a suspension of proparglyamine hydrochloride (413 mg) in pyridine was added rapidly. The mixture was warmed to room temperature and was stirred for 18 h to give a dark solution. The solvent was evaporated in vacuo to give a dark brown gum, which was dissolved in Ea/hexane/acetic acid (1:1:1% v/v) and flash chromatographed using the same solvent system to give a yellow sludge, which was triturated with ER to give the title compound as a white solid, (0.544 g), m.p. 151.5°-153°.

후처리

  1. temperatureThe solution was cooled in an ice-water bath
  2. customto give a pale brown suspension
  3. temperatureThe mixture was re-cooled in an ice-water bath
  4. additionwas added rapidly
  5. temperatureThe mixture was warmed to room temperature
  6. stirringwas stirred for 18 h
  7. customto give a dark solution
  8. customThe solvent was evaporated in vacuo
  9. customto give a dark brown gum, which
  10. custom1% v/v) and flash chromatographed
  11. customto give a yellow sludge, which
  12. customwas triturated with ER

출처 및 근거

ORD 기록
ord-43046e9f1eb749a095a56f4ec37d9ce6
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855314

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