Sodium hydride → HCID 67693623, compound

HRID 1417307

Reaction equation

HRID 1417307 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Na].Cl[CH2:17]/[CH:18]=[CH:19]/[CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31]>CN(C)C=O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:17]/[CH:18]=[CH:19]/[CH2:20][N:21]3[C:29](=[O:30])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]3=[O:31])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 823151-(p-Hydroxyphenyl)imidazoleHCID 5360545SodiumHCID 57093742-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 67693623HCID 67693623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 16.0 g of 4-(1H-imidazol-1-yl)phenol in 250 ml of dimethylformamide, is treated with 4.2 g of 60% NaH. To the suspension of the sodium salt, 23.5 g of (E)-2-[4-chloro-2-buten-1-yl)-1H-isoindole-1,3(2H)-dione is added, and the reaction mixture stirred and heated on the steam bath for 16 hours. The dimethylformamide is removed in vacuo, and the residue stirred with 250 ml of water. The insolubles are collected, washed with water, and dried. Recrystallization from ethanol gives the desired product as a solid, m.p. 170°-171° C.

Workup

  1. additionis added
  2. temperatureheated on the steam bath for 16 hours
  3. customThe dimethylformamide is removed in vacuo
  4. stirringthe residue stirred with 250 ml of water
  5. customThe insolubles are collected
  6. washwashed with water
  7. customdried
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7e2c0457e8cc4b2d85de1791618a8f7c
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Linked notes

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