Dimethylformamide → Methyl(1-((2,4-dichlorphenoxy)acetyl)-3-methyl-2-imidazolidinylidene)nitroacetate

HRID 972212

Reaction equation

HRID 972212 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[C:9]([N+:13]([O-:15])=[O:14])[C:10]([OH:12])=[O:11].[Cl:16][C:17]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:18]=1[O:19][CH2:20][C:21](Cl)=[O:22].[CH3:29]N(C)C=O>>[CH3:29][O:11][C:10](=[O:12])[C:9](=[C:5]1[N:4]([CH3:3])[CH2:8][CH2:7][N:6]1[C:21](=[O:22])[CH2:20][O:19][C:18]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:17]=1[Cl:16])[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 69887(2,4-Dichlorophenoxy)acetyl chlorideHCID 86735005(1-Methyl-2-imidazolidinylidene)nitroacetic acid

Product 1

HCID 54513855Methyl(1-((2,4-dichlorphenoxy)acetyl)-3-methyl-2-imidazolidinylidene)nitroacetate

Procedure

2.3 g of sodium hydride was slurried in 75 ml of dimethylformamide at 5°. To that slurry, at 5°, was added 19.5 g of 1B over a 30-minute period. The stirred mixture was allowed to warm to room temperature and stirred at that temperature for one hour. The mixture then was cooled to 5° and there was added thereto a solution of 25.5 g of 2,4-dichlorophenoxyacetyl chloride in 25 ml of dimethylformamide, over a 20-minute period, the stirred mixture being held at 5°-12°. The stirred mixture was allowed to warm to room temperature and stirred at that temperature overnight. The mixture then was poured into ice water. The solid was filtered, washed with water and dried by air aspiration and ether washing to give a tan-colored solid, which on recrystallization from acetonitrile gave 1, as an off-white solid, m.p.; 191°-192° (with decomposition).

Workup

  1. temperatureThe mixture then was cooled to 5°
  2. additionthere was added
  3. custombeing held at 5°-12°
  4. temperatureto warm to room temperature
  5. stirringstirred at that temperature overnight
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. dry with materialdried by air aspiration and ether washing
  9. customto give a tan-colored solid, which
  10. customon recrystallization from acetonitrile
  11. customgave 1

Sources & evidence

ORD record
ord-23f428c50188440e862d78e2954b53b6
Source dataset
uspto-grants-1977_10
Patent number
US04052411

Linked notes

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