Methyl isothiocyanate → HCID 57102878, compound

HRID 1457763Notes

Reaction equation

[CH2:1]([C:3]1[C:4](=[O:28])[N:5]([C:9]([NH:11][CH:12]2[CH2:21][C:20]3[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([S:22](=[O:25])(=[O:24])[NH2:23])[CH:19]=3)[O:14][CH2:13]2)=[O:10])[CH2:6][C:7]=1[CH3:8])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:35][N:36]=[C:37]=[S:38]>CS(C)=O>[CH2:1]([C:3]1[C:4](=[O:28])[N:5]([C:9]([NH:11][CH:12]2[CH2:21][C:20]3[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([S:22]([NH:23][C:37]([NH:36][CH3:35])=[S:38])(=[O:24])=[O:25])[CH:19]=3)[O:14][CH2:13]2)=[O:10])[CH2:6][C:7]=1[CH3:8])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

2.05 g (5 mmol) of 3-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-6-sulfamoyl-7-methoxychroman, 2.07 g (15 mmol) of finely powdered potassium carbonate and 0.44 g (6 mmol) of methyl isothiocyanate were suspended or dissolved in 20 ml of DMSO. The reaction mixture was stirred at 80° C. for 1 hour. The mixture was poured onto ice-water and the product was precipitated by acidification with hydrochloric acid. After the crude product had been filtered off with suction and dried, it was purified by chromatography over silica gel (eluting agent methylene chloride/glacial acetic acid 19:1). The product had a melting point of 205° C.

Workup

additionThe mixture was poured onto ice-water
customthe product was precipitated by acidification with hydrochloric acid
filtrationAfter the crude product had been filtered off with suction
customdried
customit was purified by chromatography over silica gel (eluting agent methylene chloride/glacial acetic acid 19:1)

Sources & evidence

ORD record: ord-72bc591da51b48688fa8e0772d51c7ad
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849755

Reaction notes

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