Methanol → Methyl 3-aminosulfonyl-4-phenoxy-5-(1-pyrrolidinyl)benzoate

HRID 1676917Notes

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4]([O:7][C:8]2[C:9]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:10][C:11]([C:18]([OH:20])=[O:19])=[CH:12][C:13]=2[S:14]([NH2:17])(=[O:16])=[O:15])=[CH:5][CH:6]=1.S(Cl)(Cl)=O.[CH3:30]O>>[NH2:17][S:14]([C:13]1[CH:12]=[C:11]([CH:10]=[C:9]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[C:8]=1[O:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:18]([O:20][CH3:30])=[O:19])(=[O:16])=[O:15]

Participants

Reactant 3

HCID 887Methanol

HCID 4849Piretanide

HCID 24386Thionyl Chloride

Product 1

HCID 11545297Methyl 3-aminosulfonyl-4-phenoxy-5-(1-pyrrolidinyl)benzoate

Procedure

In a similar manner to Example 1, piretanide can be reacted with thionyl chloride and methanol to yield methyl 3-aminosulfonyl-4-phenoxy-5-(1-pyrrolidinyl)benzoate.

Sources & evidence

ORD record: ord-3bf550064db6464596fef78adf3c6349
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008283B2

Reaction notes

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