Phosphorus pentachloride → HCID 12783772, compound

HRID 1701517Notes

Reaction equation

HRID 1701517 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](Cl)=[O:14])=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:22][N:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28]([O:30][CH3:31])=[O:29].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:22][N:23]1[CH:27]=[C:26]([C:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:14])[CH:25]=[C:24]1[C:28]([O:30][CH3:31])=[O:29]

Participants

6

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 142178Methyl 1-methylpyrrole-2-carboxylateHCID 6451240Aluminum(III) ChlorideHCID 114586874-Methoxy-1-naphthalenecarbonyl Chloride

Product 1

HCID 12783772HCID 12783772, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Methoxy-naphthoic acid chloride (35 g; prepared by action of phosphorous pentachloride on the acid of m.p. 250° C.) followed by methyl 1-methyl-pyrrole-2-carboxylate (22 g) are dissolved in 1,2-dichloroethane (400 ml). To the stirred solution, at about -20° C., is slowly added anhydrous aluminium chloride (23 g). After one hour, the resulting material is poured over 1 kg crushed ice. The organic phase is decanted off and the aqueous phase is extracted with chloroform (500 ml). The organic solution is then dried and the solvents are evaporated off. The solid residue (28 g) is washed with isopropyl ether (200 ml), to give methyl 1-methyl-4-(4-methoxy-1-naphthoyl)-pyrrole-2-carboxylate, m.p.=162° C., in a yield of 50%.

Workup

  1. customat about -20° C.
  2. additionthe resulting material is poured over 1 kg
  3. customcrushed ice
  4. customThe organic phase is decanted off
  5. extractionthe aqueous phase is extracted with chloroform (500 ml)
  6. customThe organic solution is then dried
  7. customthe solvents are evaporated off
  8. washThe solid residue (28 g) is washed with isopropyl ether (200 ml)

Sources & evidence

ORD record
ord-125fb7b7af0f4d3fbd21a82792a6316c
Source dataset
uspto-grants-1980_03
Patent number
US04194003

Reaction notes

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