2-Propanethiol → 5-Methoxy-3-[(1-methylethyl)thio]benzo[b]thiophene-2-carboxamide

HRID 2226851Notes

Reaction equation

[CH3:1][CH:2]([SH:4])[CH3:3].Cl[C:6]1[C:7]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:8]=2[S:9][C:10]=1[C:11]([NH2:13])=[O:12].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C=O)C.C(OCC)(=O)C>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:8]2[S:9][C:10]([C:11]([NH2:13])=[O:12])=[C:6]([S:4][CH:2]([CH3:3])[CH3:1])[C:7]=2[CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Propanethiol (1.1 mL, 12.4 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (3.00 g, 12.4 mmol) in 24 mL of DMF. Diazabicycloundecene (DBU) (1.8 mL, 12.4 mmol) is added and the mixture is warmed to 80° C. After 6 hours, additional amounts of 2-propanethiol (110 μL) and of DBU (180 μL) are added. Heating is continued for 1 hour. The reaction mixture is allowed to cool and then is diluted with ethyl acetate and washed with 1N NaOH, 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives 5-methoxy-3-[(1-methylethyl)thio]benzo[b]thiophene-2-carboxamide in 80% yield. An analytical sample is obtained by a second recrystallization from ethyl acetate:hexane; mp=143°-143.5° C.

Workup

temperatureHeating
waitis continued for 1 hour
temperatureto cool
washwashed with 1N NaOH, 1N HCl, water, and brine
dry with materialThe organic layer is dried over MgSO4
filtrationFiltration
concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

Sources & evidence

ORD record: ord-7b1237572fc443f8853af5bc0295dd72
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05350748

Reaction notes

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