Diethyl bromomalonate → HCID 67860713, compound

HRID 2371433Notes

Reaction equation

HRID 2371433 reaction equation
[Na].[N+:2]([C:5]1[CH:6]=[C:7]([CH3:15])[C:8]2[S:12](=[O:13])[CH:11]=[N:10][C:9]=2[CH:14]=1)([O-:4])=[O:3].Br[CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[CH3:15][C:7]1[C:8]2[S:12](=[O:13])[CH2:11][N:10]([CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:9]=2[CH:14]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=1

Participants

5

Reactant 3

HCID 69637Diethyl bromomalonateHCID 5360545SodiumHCID 67860849HCID 67860849, compound

Product 1

HCID 67860713HCID 67860713, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.69 g (0.03 g atom) of sodium is dissolved in 100 ml of ethanol. 6.3 g (0.03 mol) of 5-nitro-7-methylbenzothiazolone and then 7.17 g (0.03 mol) of diethyl bromomalonate are added to the solution. The reaction mixture is heated under reflux for 8 hours, poured onto ice and the precipitated product is recrystallized from a little ethanol. 4 g (36% of theory) of 7-methyl-5-nitro-3-(bis-ethoxycarbonyl-methyl)-benzothiazolone are obtained in the form of colorless needles of melting point 97° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 8 hours
  3. additionpoured onto ice
  4. customthe precipitated product is recrystallized from a little ethanol

Sources & evidence

ORD record
ord-1d2050ec4a86421bb5783d7c4a777528
Source dataset
uspto-grants-1992_03
Patent number
US05093345

Reaction notes

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