Methanol → HCID 14254944, compound

HRID 2352469Notes

Reaction equation

S(Cl)(Cl)=O.[CH2:5]([S:8][C:9]1[C:10]([S:17]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])=[O:18])=[C:11]([C:14]([OH:16])=[O:15])[S:12][CH:13]=1)[CH2:6][CH3:7].[CH3:25]O>>[CH2:5]([S:8][C:9]1[C:10]([S:17]([NH:20][C:21]([CH3:23])([CH3:22])[CH3:24])(=[O:19])=[O:18])=[C:11]([C:14]([O:16][CH3:25])=[O:15])[S:12][CH:13]=1)[CH2:6][CH3:7]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 14254943HCID 14254943, compound

Product 1

HCID 14254944HCID 14254944, compound

Conditions

Temperature: -10 °C

Procedure

Thionyl chloride (2.3 mL) was added dropwise to 110 mL methanol cooled to -10° C. Next 10.4 g 4-propylthio-3-(N-(1,1-dimethylethyl)aminosulfonyl)-2-thiophenecarboxylic acid was added in one portion. The solution was warmed to reflux for 6 hours, then cooled to -45° C., and the product precipitated in sufficiently pure form for the purposes of this invention; yield 8.45 g; m.p. 93°-98° C.

Workup

temperatureThe solution was warmed
temperatureto reflux for 6 hours
temperaturecooled to -45° C.
customthe product precipitated in sufficiently pure form for the purposes of this invention

Sources & evidence

ORD record: ord-495debdd00c54025ab81e6cbfde0877a
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04877440

Reaction notes

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