Triethylamine → [1,1'-Biphenyl]-3-carbonyl azide

HRID 62071

Reaction equation

HRID 62071 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][CH:28]=[C:27]([C:31](O)=[O:32])[CH:26]=1>C(O)(C)C>[C:25]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([N:15]=[N+:16]=[N-:17])=[O:32])[CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 118675061[1,1'-Biphenyl]-3-carbonyl azideYield 119.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a vial (8 mL) diphenylphosphoryl azide (0.39 mL, 1.8 mmol) and triethylamine (0.25 mL, 1.8 mmol) were added to a stirred solution of biphenyl-3-carboxylic acid (0.30 g, 1.5 mmol) in isopropanol (3 mL). The vial was closed with a lid, and the reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated, and water (50 mL) was added. The mixture was extracted with ethyl acetate (3×50 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated to provide the title compound (0.40 g, 100%) was used in the next reaction without characterization or purification.

Workup

  1. customThe vial was closed with a lid
  2. concentrationThe reaction mixture was concentrated
  3. additionwater (50 mL) was added
  4. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-59d10e76a5ef44edbf2561405cf89fbe
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Linked notes

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