Methyl bromoacetate → HCID 54374596, compound

HRID 1493606Notes

Reaction equation

HRID 1493606 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][NH:9][C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1(C)C=CC=CC=1>[NH2:12][C:10]([NH:9][N:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)=[O:11]

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 2396332-(3-Methylphenyl)hydrazine-1-carboximidic acid

Product 1

HCID 54374596HCID 54374596, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(3-methylphenyl)hydrazinecarboxamide (5 g), DEA (10.5 ml) and methyl bromoacetate (4.5 ml) in toluene (100 ml) was heated under reflux for 20 h, and was then partitioned between ethyl acetate (200 ml) and water (200 ml). The organic layer was washed with water (2×100 ml) and saturated brine (100 ml) before being dried and evaporated in vacuo to leave an oil (6.1 g). This was purified by FCC eluting with ethyl acetate to give the title compound (4.4 g) as a solid, m.p. 68°-70° after recrystallisation from ethyl acetate and trituration with ether.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. customwas then partitioned between ethyl acetate (200 ml) and water (200 ml)
  4. washThe organic layer was washed with water (2×100 ml) and saturated brine (100 ml)
  5. custombefore being dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c71c63a4a3a84c258c9c3d1d6f7a188f
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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