Sodium hydride → 5-phenyl-2,4-pentadienyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetate

HRID 442302노트

반응식

HRID 442302 반응식
[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N+:15]([C:18](=[C:23]1[NH:28][CH2:27][CH2:26][CH2:25][S:24]1)[C:19](OC)=[O:20])([O-:17])=[O:16]>CN(C)C=O>[N+:15]([C:18](=[C:23]1[NH:28][CH2:27][CH2:26][CH2:25][S:24]1)[C:19]([O:12][CH2:11][CH:10]=[CH:9][CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:20])([O-:17])=[O:16]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 534270135-Phenyl-2,4-PentadienolHCID 71400745Methyl nitro(1,3-thiazinan-2-ylidene)acetate

생성물 1

HCID 737915515-phenyl-2,4-pentadienyl nitro(tetrahydro-2H-1,3-thiazin-2-ylidene)acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 8.0 g of 5-phenyl-2,4-pentadien-1-ol in 30 ml of dimethylformamide (DMF) was added dropwise over a 30-minute period to a mixture of 1.5 g of sodium hydride and 20 ml of DMF, at 5°. The mixture was stirred for 1 hour at 5°. Then 3.3 g of 1A was added to the stirred mixture at 5° and the resulting mixture was stirred for three hours. The mixture then was poured into ice water and extracted with ether, and the aqueous phase was separated, acidified with acetic acid and extracted with methylene chloride. The methylene chloride extracts were washed with water, dried (MgSO4), and stripped of solvent. The residue was triturated in water and then ether, to give a solid which on recrystallization from ethanol gave 1, as a yellow solid, m.p.: 123°-125°.

후처리

  1. stirringthe resulting mixture was stirred for three hours
  2. extractionextracted with ether
  3. customthe aqueous phase was separated
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customThe residue was triturated in water
  8. customether, to give a solid which
  9. customon recrystallization from ethanol
  10. customgave 1

출처 및 근거

ORD 기록
ord-d04884989a654a5985f0716db31c154a
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04045434

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