p-Toluenesulfonic acid → HCID 66744039, compound

HRID 2364016Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:9].[O-]S([O-])(=O)=O.[Mg+2].CO[C:28](OC)([CH3:30])[CH3:29].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Br:7][C:5]1[S:4][C:3]2[C:8](=[O:9])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:28]([CH3:30])([CH3:29])[NH:1][C:2]=2[CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-amino-5-bromo-N-(4-methoxybenzyl)thiophene-2-carboxamide (160 mg, 0.47 mmol), MgSO4 (60 mg), 2,2-dimethoxypropane (0.5 mL), PTSA (8.6 mg, 0.050 mmol) and DMA (0.5 mL) was stirred at 120° C. for 1 h by using microwave reactor. Then, the mixture was poured into saturated aqueous NaHCO3. The organic materials were extracted with AcOEt. The combined extracts were washed with water and brine, and then dried over Na2SO4. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (silica gel, 90:10 hexane/EtOAc to 40:60 hexane/EtOAc) to give the title compound (112 mg, 62%) as a pale brown solid:

Workup

extractionThe organic materials were extracted with AcOEt
washThe combined extracts were washed with water and brine
dry with materialdried over Na2SO4
customAfter removal of the solvent at reduced pressure
customthe residue was purified by column chromatography (silica gel, 90:10 hexane/EtOAc to 40:60 hexane/EtOAc)

Sources & evidence

ORD record: ord-2ffecb84bac647cd9ecfd63739755cc0
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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