Chloride → HCID 3428627, compound

HRID 483876Notes

Reaction equation

HRID 483876 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[Cl-]>C(Cl)Cl.O>[Cl:1][CH2:2][C:3]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[O:4]

Participants

6

Reactant 3

HCID 312ChlorideHCID 6577Chloroacetyl chlorideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 3428627HCID 3428627, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14.9 g of chloroacetyl chloride in 25 ml of methylene chloride was added to a stirred solution of 15.0 g of 1-(3-aminopropyl)imidazole in 75 ml of methylene chloride at 0° C. The rate of addition was controlled to keep the reaction temperature below 15° C. During the course of the reaction a brown gummy viscous oil separated out of solution. Approximately two-thirds of the way through the addition, 50 ml of 20% NaOH was added to the mixture, and the oil went into solution. After the addition was completed, the mixture was stirred at room temperature for 15 minutes. The water layer was removed, the organic layer was dried over MgSO4 and filtered, and the solvent was removed under vacuum to give a yellow oil. The oil was dissolved in 30 ml of water and the pH was adjusted to approximately 3.0. Analysis for organic chloride indicated dimerization and/or trimerization had occurred.

Workup

  1. additionThe rate of addition
  2. customthe reaction temperature below 15° C
  3. customDuring the course of the reaction a brown gummy viscous oil
  4. customseparated out of solution
  5. additionApproximately two-thirds of the way through the addition, 50 ml of 20% NaOH
  6. additionwas added to the mixture
  7. additionAfter the addition
  8. customThe water layer was removed
  9. dry with materialthe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. customthe solvent was removed under vacuum
  12. customto give a yellow oil

Sources & evidence

ORD record
ord-e78ea69143444086a248f5df2dd75840
Source dataset
uspto-grants-1993_07
Patent number
US05227481

Reaction notes

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