Dimethylformamide → HCID 15572341, compound

HRID 2286587Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:15][CH:16]=[CH:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=1.[OH-].[Na+].CN([CH:32]=[O:33])C>>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[CH:17]=[C:16]([CH:32]=[O:33])[NH:15][C:14]=2[C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=2)=[CH:20][CH:21]=1

Participants

Reactant 4

HCID 6228Dimethylformamide2×

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 13340632HCID 13340632, compound

Product 1

HCID 15572341HCID 15572341, compoundYield 55%

Procedure

To 25 ml DMF at 0° was added dropwise with stirring 30 g of phosphorus oxychloride. The mixture was stirred for 15 minutes at room temperature, then a solution of 5.6 g (0.02 mole) of 2,3-bis(4-methoxyphenyl)pyrrole in 40 ml DMF was added dropwise with cooling in an ice bath. The mixture was then heated at 70°-80° for one hour, then cooled. Aqueous sodium hydroxide (50%) was added until the mixture was basic. The reaction mixture was then heated again at 70° for 15 minutes. The cooled reaction mixture was poured into ice water. The precipitated material was collected and purified by chromatography on 600 g Silic AR CC-7 (eluting with toluene containing 1-2% ethyl acetate) to give 3.4 g (55%) of product, m.p. 165°-6° (methylcyclohexane/toluene).

Workup

temperaturewith cooling in an ice bath
temperatureThe mixture was then heated at 70°-80° for one hour
temperaturecooled
temperatureThe reaction mixture was then heated again at 70° for 15 minutes
customThe cooled reaction mixture
customThe precipitated material was collected
custompurified by chromatography on 600 g Silic AR CC-7 (eluting with toluene containing 1-2% ethyl acetate)

Sources & evidence

ORD record: ord-336026348b3e456b97c8481a591a0dab
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04267184

Reaction notes

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