Dimethylformamide → 3-(1-Cyano-1-methylethyl)benzoyl chloride

HRID 1800414Notes

Reaction equation

HRID 1800414 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](O)=[O:10])([CH3:5])[CH3:4])#[N:2].C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>O1CCCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([Cl:18])=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acid

Product 1

HCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (53 mg, 0.280 mmol) produced in Example B2(x) in tetrahydrofuran (2.0 mL) were added oxalyl chloride (35 μL, 0.42 mmol) and N,N-dimethylformamide (about 20 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure to give 3-(1-cyano-1-methylethyl)benzoyl chloride as a pale-brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b3a91d0c045c42748c359a48f94be620
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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