Triethylamine → HCID 19096820, compound

HRID 487026Notes

Reaction equation

[CH2:1]([CH:4]1[CH2:6][C:5]1([C:11]([O-:13])=O)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3].ClC(OCC)=O.[Br:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[C:23]([CH3:28])[CH:22]=1.C(N(CC)CC)C>>[Br:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:11]([C:5]2([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH:4]2[CH2:1][CH2:2][CH3:3])=[O:13])=[C:23]([CH3:28])[CH:22]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

HCID 114234-Bromo-2-methylaniline

HCID 85670809HCID 85670809, compound

Product 1

HCID 19096820HCID 19096820, compoundYield 53.8%

Procedure

Monomethyl 2-(n-propyl)cyclopropane-1,1-dicarboxylate (2.47 grams, 0.013 mole) from Part B, above, ethyl chloroformate (1.44 grams, 0.013 mole) and 4-bromo-2-methylaniline (2.48 grams, 0.013 mole) were reacted sequentially in the presence of triethylamine (1.35 grams, 0.013 mole) in a manner similar to that described In Example XXXIII to give 2.43 grams (0.007 mole) of methyl 1-(4-bromo-2-methyl-phenylaminocarbonyl)-2-n-propylcyclopropanecarboxylate having a melting point of 60° C.-66° C. Elemental analysis of the product indicated the following:

Sources & evidence

ORD record: ord-37a9a341187f4ff9a0f265f098a15c30
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292937

Reaction notes

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