Cyclopropanecarbonyl chloride → N-(4-chloro-3-nitrobenzyl)cyclopropanecarboxamide

HRID 59291Notes

Reaction equation

HRID 59291 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[CH:14]1([C:17](Cl)=[O:18])[CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:17]([CH:14]2[CH2:16][CH2:15]2)=[O:18])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 18796739(4-Chloro-3-nitrobenzyl)amine hydrochloride

Product 1

HCID 90019905N-(4-chloro-3-nitrobenzyl)cyclopropanecarboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure as described in step-2 of Intermediate-30 by using (4-chloro-3-nitrophenyl)methanamine hydrochloride (0.700 g, 3.14 mmol), cyclopropylcarbonyl chloride (0.490 g, 4.71 mmol), DIPEA (3.0 mL) and THF (15 mL) to afford 0.400 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.69 (d, J=6.0 Hz, 2H), 1.55-1.61 (m, 1H), 4.33 (d, J=6.0 Hz), 7.55 (d, J=7.8 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.87 (s, 1H), 8.68 (br s, 1H); MS (m/z): 255.09 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a7db810ef4cf46b8915b4d4866ed3fd9
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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