Dimethylformamide → 2-Chloro-N-cyclopropyl-5-(3-methoxy-propyl)-benzamide

HRID 1715392Notes

Reaction equation

[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][CH2:16][O:17][CH3:18])=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].CN(C=O)C.C1(S(NN)(=O)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:8][CH2:9]1)=[O:5]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Chloro-N-cyclopropyl-5-(3-methoxy-propenyl)-benzamide (12.6 g, 47.6 mmol) was dissolved in dry toluene (650 mL). Dry DMF (70 mL) was added, and the mixture was heated to 110° C. Benzensulfonyl hydrazine (24.5 g, 143 mmol) was added in three portions over 3 h. The mixture was heated for a total time of 3 h, and allowed to cool to rt. The solvents were removed under reduced pressure, and the residue was diluted with Et2O. The mixture was washed with water, and the aq. phase was extracted back with Et2O (3×). The combined org. extracts were washed with water, and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:9→1:4→1:3→1:1) yielded the title compound (10.0 g, 78%). LC-MS: tR=0.83 min; ES+: 268.19.

Workup

temperatureThe mixture was heated for a total time of 3 h
temperatureto cool to rt
customThe solvents were removed under reduced pressure
additionthe residue was diluted with Et2O
washThe mixture was washed with water
extractionthe aq. phase was extracted back with Et2O (3×)
washextracts were washed with water, and brine
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (EtOAc/heptane 1:9→1:4→1:3→1:1)

Sources & evidence

ORD record: ord-4950fba2cf434396949e9f3844143318
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799805B2

Reaction notes

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