Diethyl Sulfate → HCID 12495247, compound

HRID 1730632Notes

Reaction equation

[CH2:1](OS(OCC)(=O)=O)[CH3:2].[C:10]([C:18]1[C:19]([N:30]([CH2:41][CH3:42])S(C2C=CC(C)=CC=2)(=O)=O)=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:21][C:22]=1[CH3:23])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:10]([C:18]1[C:19]([NH:30][CH2:41][CH3:42])=[C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:21]([CH2:1][CH3:2])[C:22]=1[CH3:23])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 6163Diethyl Sulfate

HCID 54358704HCID 54358704, compound

Product 1

HCID 12495247HCID 12495247, compound

Procedure

Compound B) is transformed into the corresponding p-toluene sulfonamido derivative (M.p. 230°-33° C) by reaction with p-toluenesulfonychloride. This compound is subsequently reacted in strong alkaline solution with diethylsulfate, thus obtaining 4-benzoyl-3-(N-ethyl-p-toluenesulfonamido)-5-methyl-2-phenyl-pyrrole (M.p. 152°-53° C), which is in turn converted into the title compound (B.p. 220° C/0.015 mmHg) by acid hydrolysis.

Sources & evidence

ORD record: ord-edff8aefdb01463c82fcfe7f6bd11596
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03993650

Reaction notes

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