Triethylamine → HCID 55034656, compound

HRID 2060738Notes

Reaction equation

[C:1]1([C:7]([OH:9])=[O:8])([C:4](O)=[O:5])[CH2:3][CH2:2]1.CCN(CC)CC.S(Cl)(Cl)=O.[F:21][C:22]1[CH:29]=[CH:28][C:25]([NH:26][CH3:27])=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:29]=[CH:28][C:25]([N:26]([CH3:27])[C:4]([C:1]2([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]2)=[O:5])=[CH:24][CH:23]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 24386Thionyl Chloride

HCID 680244-Fluoro-N-methylaniline

HCID 690171,1-Cyclopropanedicarboxylic acid

Product 1

HCID 55034656HCID 55034656, compoundYield 80.6%

Procedure

Using a procedure analogous to Example B1, 1,1-cyclopropanedicarboxylic acid (2 g, 15.37 mmol), Et3N (2.14 mL, 15.4 mmol), thionyl chloride (1.12 mL, 15.4 mmol), and 4-fluoro-N-methylaniline (1.83 g, 14.6 mmol) were combined to provide 1-((4-fluorophenyl)(methyl)carbamoyl)cyclopropanecarboxylic acid (2.79 g, 72% yield). MS (ESI) m/z: 260.0 (M+Na+).

Sources & evidence

ORD record: ord-e5141a587d034a1481794c3e46f55251
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278331B2

Reaction notes

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