Dimethylformamide → HCID 23452888, compound

HRID 2049916Notes

Reaction equation

HRID 2049916 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:24]=[C:25]([C:30]([OH:32])=[O:31])[C:26]=1[N+:27]([O-:29])=[O:28])[O:7][CH2:8][C:9]([N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:10])([OH:3])=[O:2].CN(C)[CH:35]=[O:36].[CH3:38][O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Cl)=[CH:42][CH:41]=1>C(N(CC)CC)C>[CH3:38][O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][O:31][C:30]([C:25]2[CH:24]=[C:6]([CH:5]=[C:4]([C:1]([O:3][CH2:1][C:4]3[CH:5]=[CH:6][C:24]([O:36][CH3:35])=[CH:25][CH:26]=3)=[O:2])[C:26]=2[N+:27]([O-:29])=[O:28])[O:7][CH2:8][C:9]([N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:10])=[O:32])=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 699934-Methyloxybenzyl chlorideHCID 23452868HCID 23452868, compound

Product 1

HCID 23452888HCID 23452888, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (3,5-dicarboxy-4-nitrophenoxy)-N,N-dihexylacetamide in dimethylformamide containing two equivalents of triethylamine are added two equivalents of p-methoxybenzylchloride. The mixture is stirred and heated to about 100° C. for 1 hr. After this time, the reaction is cooled to room temperature and poured into ice water. The aqueous mixture is extracted with 2 portions of methylene chloride. The combined extracts are back-extracted with water to remove dimethylformamide, dried over anhydrous calcium sulfate, filtered and concentrated under reduced pressure. The remaining oil which was not induced to crystallize is analyzed by NMR and used directly in the next step.

Workup

  1. temperatureAfter this time, the reaction is cooled to room temperature
  2. extractionThe aqueous mixture is extracted with 2 portions of methylene chloride
  3. extractionThe combined extracts are back-extracted with water
  4. customto remove dimethylformamide
  5. dry with materialdried over anhydrous calcium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto crystallize

Sources & evidence

ORD record
ord-ee03ef13e3e54764bd7ae731aade9a62
Source dataset
uspto-grants-1980_04
Patent number
US04199354

Reaction notes

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