Nitrogen → 3',4',5'-Trimethoxy-biphenyl-2-carbonyl chloride

HRID 383611Notes

Reaction equation

HRID 383611 reaction equation
N#N.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:15]2[C:16]([C:21]([OH:23])=O)=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12].C(Cl)(=O)C([Cl:27])=O>C(Cl)Cl.CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:15]2[C:16]([C:21]([Cl:27])=[O:23])=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 947NitrogenHCID 65578Oxalyl chlorideHCID 597857043',4',5'-Trimethoxy-biphenyl-2-carboxylic acid

Product 1

HCID 161162893',4',5'-Trimethoxy-biphenyl-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 3′,4′,5′-Trimethoxy-biphenyl-2-carboxylic acid (83) (54 mg, 0.18 mmol) in anhydrous DCM (1.3 mL) and add anhydrous DMF (1 drop, cat. amount). Then add slowly oxalyl chloride (21 μL, 0.24 mmol) by keeping temperature at ca. 20° C. with a water bath and stir the turbid mixture for additional 2 h at rt. Remove solvent and dry in vacuum to obtain crude 3′,4′,5′-Trimethoxy-biphenyl-2-carbonyl chloride (84) as a yellow solid. No further purification.

Workup

  1. custom(The following reaction
  2. customat ca. 20° C.
  3. customRemove solvent and dry in vacuum

Sources & evidence

ORD record
ord-ff56853765b446a3bbf49dfeccdfb014
Source dataset
uspto-grants-2013_02
Patent number
US08367677B2

Reaction notes

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