Dimethylformamide → HCID 21426439, compound

HRID 258702Notes

Reaction equation

HRID 258702 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[S:7]([C:11]1[N:12]([CH2:16][C:17]([OH:19])=O)[CH:13]=[CH:14][N:15]=1)([CH3:10])(=[O:9])=[O:8].CN(C)C=O>C(Cl)Cl>[S:7]([C:11]1[N:12]([CH2:16][C:17]([Cl:2])=[O:19])[CH:13]=[CH:14][N:15]=1)([CH3:10])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24819Phosphorus pentachlorideHCID 21426444HCID 21426444, compound

Product 1

HCID 21426439HCID 21426439, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

Phosphorus pentachloride (22.5 g.) dissolved in methylene chloride (150 cc.) is added dropwise and whilst cooling to 5° C., to a suspension of (2-mesyl-imidazol-1-yl)-acetic acid (12.3 g.) in methylene chloride (50 cc.). Dimethylformamide (2 cc.) is added thereafter and the mixture is then heated under reflux for 4 hours. The mixture is cooled to 10° C., the resulting solid is filtered off and washed with methylene chloride (15 ac.) to give (2-mesyl-imidazol- 1 -yl)-acetyl chloride (12.4 g.), m.p. 132°-133° C.

Workup

  1. additionis added dropwise
  2. temperaturethe mixture is then heated
  3. temperatureunder reflux for 4 hours
  4. filtrationthe resulting solid is filtered off
  5. washwashed with methylene chloride (15 ac.)

Sources & evidence

ORD record
ord-bba483467fe846e69d8bc65b5c5bb971
Source dataset
uspto-grants-1977_07
Patent number
US04034088

Reaction notes

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