Triethylamine → HCID 765824, compound

HRID 1953247Notes

Reaction equation

HRID 1953247 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][C:21]=1[N+:29]([O-:31])=[O:30]>O1CCCC1>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:25])=[CH:22][C:21]=1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86401-NaphthylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 765824HCID 765824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.8 g (0.02 mol) of 1-naphthylamine and 2.0 g (0.02 mol) of triethylamine in 50 ml tetrahydrofuran is added dropwise at 15-20° C. a solution of 4.4 g (0.02 mol) of 4-chloro-3-nitro-benzoic acid chloride in 20 ml tetrahydrofuran. The solution is stirred for 30 minutes at ambient temperature. Then the solvent is evaporated off and the residue is chromatographed on silica gel, eluting with methylene chloride. The desired fractions are concentrated by evaporation, triturated with ether, suction filtered and dried.

Workup

  1. customThen the solvent is evaporated off
  2. customthe residue is chromatographed on silica gel
  3. washeluting with methylene chloride
  4. concentrationThe desired fractions are concentrated by evaporation
  5. customtriturated with ether, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-bc75fc3d23fe46c69385ab37159fecec
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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