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Dimethylformamide → 2-Sulfo-2-(1-pyrryl)acetyl chloride

HRID 26319
Notes
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Reaction equation

HRID 26319 reaction equation
[S:1]([CH:5]([N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[C:6](O)=[O:7])([OH:4])(=[O:3])=[O:2].S(Cl)([Cl:16])=O.CN(C)C=O.CCCCCC>CCOCC>[S:1]([CH:5]([N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[C:6]([Cl:16])=[O:7])([OH:4])(=[O:3])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 24386Thionyl ChlorideHCID 867364652-Sulfo-2-(1-pyrryl)acetic acid

Product 1

HCID 867364672-Sulfo-2-(1-pyrryl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Conditions

Temperature
40 °C

Procedure

2-Sulfo-2-(1-pyrryl)acetic acid is treated with thionyl chloride in ether at room temperature according to the general procedure in J. Med. Chem., 15, 1105 (1972) until the evolution of gas stops. Dimethylformamide is added, the solution is warmed to about 40° C. for 1 hour. Then ether is added, followed by hexane and the solution cooled to about -25° C. 2-Sulfo-2-(1-pyrryl)acetyl chloride is isolated from the solvent by decantation.

Workup

  1. temperaturethe solution cooled to about -25° C

Sources & evidence

ORD record
ord-e1561fb8a76442beaa3c4d1d9f935f62
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04148998

Reaction notes

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