Thionyl Chloride → 3,4-Dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride

HRID 1948352Notes

Reaction equation

[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9](N[C@@H]1CCN(C2SC(C([O-])=O)=CN=2)C[C@@H]1F)=[O:10].OCC(CO)([NH3+])CO.O=S(Cl)[Cl:37]>>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([Cl:37])=[O:10]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 685177971,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylate2×

Product 1

HCID 860383943,4-Dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride

Procedure

A solution of 10.4 g (54 mmol) of 3,4-Dichloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 1) in 100 ml SOCl2 was heated at reflux for 30 min. Solvent was removed to afford product. NMR (CDCl3): 2.3 (s, 1H), 8.8 (s, 1H).

Workup

temperatureat reflux for 30 min
customSolvent was removed
customto afford product

Sources & evidence

ORD record: ord-aa3355fd84c54e2cbb66491abc09bce1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399489B2

Reaction notes

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