Sodium hydride → HCID 13531657, compound

HRID 653106Notes

Reaction equation

HRID 653106 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([N+:9]([O-:11])=[O:10])[O:8][C:4]=2[CH:3]=1.[H-].[Na+].Cl.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][Cl:27]>C(COC)OC>[ClH:27].[CH3:23][N:24]([CH2:25][CH2:26][O:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([N+:9]([O-:11])=[O:10])[O:8][C:4]=2[CH:3]=1)[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 20195525HCID 20195525, compound

Product 1

HCID 13531657HCID 13531657, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 2 g. (0.008 mole) of 6-hydroxy-2-nitro-3-phenylbenzofuran (described in U.S. Pat. No. 3,927,037, Example 2) in 25 ml. of glyme is added a solution of 0.016 mole of sodium hydride in 20 ml. of glyme. To this solution is added 1.2 g. (0.008 mole) of N,N-dimethyl-N-(2-chloroethyl)amine hydrochloride. The mixture is heated to its reflux temperature and maintained at reflux for 6 hours. The reaction mixture is extracted thrice with diethyl ether, the ether is washed with water and saturated sodium chloride solution and then dried. The ether extracts are treated while stirring with hydrogen chloride gas. A yellow residue is separated and washed with diethyl ether, then recrystallized from isopropanol to provide N,N-dimethyl-2-(2-nitro-3-phenyl-6-benzofuranyloxy)ethylamine hydrochloride, m.p. 231°-235° C. (dec.), having the structure

Workup

  1. additionTo this solution is added 1.2 g
  2. temperatureThe mixture is heated to its
  3. temperaturereflux temperature
  4. temperaturemaintained
  5. temperatureat reflux for 6 hours
  6. extractionThe reaction mixture is extracted thrice with diethyl ether
  7. washthe ether is washed with water and saturated sodium chloride solution
  8. customdried
  9. additionThe ether extracts are treated
  10. customA yellow residue is separated
  11. washwashed with diethyl ether
  12. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-da730934931d4d9ca925a3d99ae2eb26
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

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