Methane → 3-(5-Fluoro-2-methoxybenzamido)-6-(methylaminothiocarbonylaminosulfonyl)-7-methoxychroman

HRID 1457750Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]=[C:9]=[S:10].[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:41][CH3:42])=[C:16]([CH:40]=1)[C:17]([NH:19][CH:20]1[CH2:29][C:28]2[C:23](=[CH:24][C:25]([O:38][CH3:39])=[C:26]([S:30]([NH:33]C(NC)=O)(=[O:32])=[O:31])[CH:27]=2)[O:22][CH2:21]1)=[O:18].C>CS(C)=O>[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:41][CH3:42])=[C:16]([CH:40]=1)[C:17]([NH:19][CH:20]1[CH2:29][C:28]2[C:23](=[CH:24][C:25]([O:38][CH3:39])=[C:26]([S:30]([NH:33][C:9]([NH:8][CH3:7])=[S:10])(=[O:32])=[O:31])[CH:27]=2)[O:22][CH2:21]1)=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

1.65 g (12 mmol) of powdered potassium carbonate and 0.35 g (4.8 mmol) of methyl isothiocyanate were added to 1.64 g (4 mmol) of 3-(5-fluoro-2-methoxybenzamido)-6-sulfamoyl-7-methoxychroman (Example 9) in 10 ml of dry DMSO. After the mixture had been stirred at 80° C. for 25 minutes, it was cooled, introduced into ice-water, clarified with charcoal and acidified to pH 1. The precipitate was filtered off with suction, dried and recrystallized from ethanol. The product had a melting point of 221°-222° C.

Workup

temperatureit was cooled
filtrationThe precipitate was filtered off with suction
customdried
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-ace4aea548f84b5bba6fdc91055c3db6
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849755

Reaction notes

Loading…