Triethylamine → HCID 91659208, compound

HRID 588905Notes

Reaction equation

HRID 588905 reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.CC[N:17](CC)CC.ClC(OCC)=O.N.O>C1COCC1>[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH2:17])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12896473Azane;hydrateHCID 754856834-Bromo-5-chloro-2-nitrobenzoic acid

Product 1

HCID 91659208HCID 91659208, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-bromo-5-chloro-2-nitrobenzoic acid (1.3 g, 4.63 mmol), Et3N (1.4 g, 13.9 mmol) in THF (20 mL) at 0° C., ethyl chloroformate (1.5 g, 13.9 mmol) was added. The resulting mixture was stirred at 0° C. for 1 h. Then NH3.H2O (4 mL) was added and stirred for 0.5 h. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the crude product (900 mg).

Workup

  1. stirringstirred for 0.5 h
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf43d9f56d5b4d189310b7ce47817a7c
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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