p-Acetamidobenzoic acid → 4-Acetamidobenzoyl chloride

HRID 1632021Notes

Reaction equation

HRID 1632021 reaction equation
ClC1C=C(C2C(OC)=CC=C([C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)=[O:17])C=2F)C=CC=1.C(NC1C=CC(C(O)=O)=CC=1)(=O)C.O=S(Cl)[Cl:44]>C1COCC1.CN(C=O)C>[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([Cl:44])=[O:17])=[CH:19][CH:20]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 19266p-Acetamidobenzoic acidHCID 24386Thionyl ChlorideHCID 58019879HCID 58019879, compound

Product 1

HCID 70103414-Acetamidobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Synthesis of N-[4-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-carbonyl)-phenyl]-acetamide (I-19, R1═CH3, R2═Cl, Y═F, R3=4-acetylaminophenyl): To a stirred suspension of 4-acetylaminobenzoic acid (Aldrich, 1.32 g, 5.58 mmol) in anhydrous THF (20 mL) was added SOCl2 (1.19 g, 10.04 mmol) and DMF (4 drops). The reaction mixture was stirred at room temperature for 3 h, concentrated under vacuum to afford 4-acetylaminobenzoyl chloride (I-18, R3=4-acetylaminophenyl) as a light yellow solid.

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-51a74179546840fc8ea93abfaaa69918
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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