Triethylamine → HCID 59656668, compound

HRID 2054898Notes

Reaction equation

HRID 2054898 reaction equation
[C:1]([C:3]1[C:4]([F:15])=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:6](O)=[O:7])#[N:2].C(N(CC)CC)C.ClC(OCC)=O.[N-:29]=[N+:30]=[N-:31].[Na+]>C1COCC1.C(Cl)Cl.O.CCOC(C)=O>[C:1]([C:3]1[C:4]([F:15])=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:6]([N:29]=[N+:30]=[N-:31])=[O:7])#[N:2]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 59656658HCID 59656658, compound

Product 1

HCID 59656668HCID 59656668, compoundYield 74.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the above benzoic acid intermediate (3 g, 14.34 mmol) and triethylamine (4.5 g, 44.47 mmol) in dry THF (30 mL) at −10° C. was added ethyl chloroformate (2.5 g, 23.04 mmol). The reaction was stirred for 1 h and monitored by TLC (20% EtOAc in CH2Cl2). A solution of NaN3 (2.3 g, 35.34 mmol) in water (15 mL) was added dropwise to the mixture and stirred for 2 h. The mixture was diluted with water (40 mL) and extracted with toluene (3×20 mL). The extract was washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give 3-cyano-4-ethoxy-2-fluoro-benzoyl azide (2.5 g, 39.2%).

Workup

  1. stirringstirred for 2 h
  2. extractionextracted with toluene (3×20 mL)
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ca1affbac37f46cda93c18b53fa25a6b
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

Loading…