Sodium hydride → HCID 20515465, compound

HRID 1902483Notes

Reaction equation

HRID 1902483 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[C:18]([CH3:19])=[CH:17][N:16]([CH3:20])[C:15]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH3:20][N:16]1[CH:17]=[C:18]([CH3:19])[C:14]([NH:13][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N+:10]([O-:12])=[O:11])=[C:15]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 20515479HCID 20515479, compound2×

Product 1

HCID 20515465HCID 20515465, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

The solution of ethyl 3-amino-1,4-dimethyl-1H-pyrrole-2-carboxylate in dimethyl formamide obtained in Example 19 is cooled to 0° C.; 3.0 g of 80% sodium hydride and 14.1 g of 2-fluoronitrobenzene are added thereto with stirring. After removing the ice-bath, the temperature rises to 40° C. and, simultaneously, an evolution of gas can be observed; this evolution subsides after 3 hours. The mixture is stirred overnight, cooled to 0° C.; 100 g of ice and 100 ml of water are then added. The precipitate formed is filtered off and is washed thoroughly with cold (0° C.) methanol. 13.5 g (87%) of the title compound of m.p. 114° C. (from ethanol) are obtained.

Workup

  1. customAfter removing the ice-bath
  2. customrises to 40° C.
  3. stirringThe mixture is stirred overnight
  4. addition100 g of ice and 100 ml of water are then added
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washis washed thoroughly with cold (0° C.) methanol

Sources & evidence

ORD record
ord-4e4ac2db8c0a48969d5624355f3299fe
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Reaction notes

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