Hydrochloric Acid → HCID 18551200, compound

HRID 1266434Notes

Reaction equation

HRID 1266434 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:14]([NH2:17])[CH:15]=[CH2:16].S(Cl)(Cl)=O.Cl>O1CCCC1.C(OCC)(=O)C>[CH2:14]([NH:17][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[Br:1])[CH:15]=[CH2:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 24386Thionyl Chloride2×HCID 3135342-Bromo-4-nitrobenzoic acid

Product 1

HCID 18551200HCID 18551200, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5 g of 2-bromo-4-nitrobenzoic acid is converted into acid chloride, which is dissolved in 50 ml of tetrahydrofuran and added in drops to 3 ml of allylamine in 20 ml of tetrahydro-furan, by 2 hours of boiling with 30 ml of thionyl chloride and distilling-off of excess thionyl chloride. After 20 hours at room temperature, it is dispersed between 1N hydrochloric acid and ethyl acetate, the ethyl acetate phase is washed with water, dried (Na2SO4) and concentrated by evaporation. The residue is crystallized with hexane. 5.6 g of 2-bromo-4-nitrobenzoic acid-allylamide, melting point 98-100° C., is obtained.

Workup

  1. washthe ethyl acetate phase is washed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customThe residue is crystallized with hexane

Sources & evidence

ORD record
ord-d0bd8d9d807043eba9ac2238d7bf385d
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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