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

HRID 442302ノート

反応式

HRID 442302 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-d04884989a654a5985f0716db31c154a
出典データセット
uspto-grants-1977_08
特許番号
US04045434

反応ノート

読み込み中…