Benzoyl chloride → HCID 19016562, compound

HRID 1728647Notes

Reaction equation

HRID 1728647 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([C:17]#[N:18])=[C:6]([Cl:16])[NH:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.CN(C)P(N(C)C)(N(C)C)=O.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.O.C(OCC)C>[C:30]([N:7]1[C:8]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[C:4]([Br:3])[C:5]([C:17]#[N:18])=[C:6]1[Cl:16])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 190165614-Bromo-2-chloro-5-(4-chlorophenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 19016562HCID 19016562, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (0.21 g of a 60% dispersion, 5.3 mmol) in 50 mL of dry tetrahydrofuran in a 100 mL single neck round bottom flask fitted with a condenser and a nitrogen inlet is added portionwise 4-bromo-2-chloro-5-(p-chlorophenyl)pyrrole-3-carbonitrile (1.0 g, 3.2 mmol). The reaction is stirred for 15 minutes at room temperature before the pipette addition of hexamethylphosphoramide (HMPA) (3 mL) followed immediately by benzoyl chloride (0.75 g, 5.4 mmol). Thereafter the reaction mixture is heated to reflux for 17 hours and allowed to cool. Rotary evaporation yields a crude semi-solid to which is added 15 mL of diethyl ether and 15 mL of water. Vigorous stirring over a period of 20 minutes followed by vacuum filtration results in the isolation of the product as a yellow solid (1.0 g, 2.4 mmol, 75%), mp 179°-181° C.

Workup

  1. customfitted with a condenser and a nitrogen inlet
  2. temperatureThereafter the reaction mixture is heated
  3. temperatureto reflux for 17 hours
  4. temperatureto cool
  5. customRotary evaporation
  6. customyields a crude semi-solid to which
  7. filtrationfollowed by vacuum filtration

Sources & evidence

ORD record
ord-0d1766de8a9640d7a73e10a31e940919
Source dataset
uspto-grants-1994_07
Patent number
US05328928

Reaction notes

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