Phosgene → HCID 22145377, compound

HRID 977011Notes

Reaction equation

HRID 977011 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH2:11][OH:12])[N:5]=1)(=[O:3])[CH3:2].[C:13](Cl)([Cl:15])=[O:14]>ClCCl.C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH2:11][O:12][C:13]([Cl:15])=[O:14])[N:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 22145372HCID 22145372, compound

Product 1

HCID 22145377HCID 22145377, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

3-Acetyl-1-(2-hydroxyethyl)-5-methylpyrazole (505 mg, prepared as described in Example 12, Preparation 1) in dry dichloromethane (5 ml) under an atmosphere of argon was treated with a solution of phosgene in toluene (12.5% w/w, 5.22 ml) and the mixture stirred for 1.5 h. The solvents were then removed, dichloromethane was added and removed using a rotary evaporator to give 3-acetyl-1-[2-(chlorocarbonyloxy)ethyl]-5-methylpyrazole; νmax (CH2Cl2) 1777 and 1684 cm-1.

Workup

  1. customThe solvents were then removed
  2. additiondichloromethane was added
  3. customremoved
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-58f6cc8afa2f4b938f7c46eb6ee4f500
Source dataset
uspto-grants-1997_03
Patent number
US05612477

Reaction notes

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