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

HRID 2075937Notes

Reaction equation

HRID 2075937 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 (56) (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 (57) 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-5db843ebe6934c4b9635130950a006f0
Source dataset
uspto-grants-2011_04
Patent number
US07923473B2

Reaction notes

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