Hydrochloric Acid → HCID 18551200, compound

HRID 1698822Notes

Reaction equation

HRID 1698822 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-b7d5371e9dbc42459c242fab7c57d946
Source dataset
uspto-grants-2002_02
Patent number
US06344454B1

Reaction notes

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