Formaldehyde → HCID 53742100, compound

HRID 1448663Notes

Reaction equation

HRID 1448663 reaction equation
[CH:1]([O:4][C:5]([C:7]1[NH:8][C:9]([Cl:13])=[C:10]([Cl:12])[N:11]=1)=[O:6])([CH3:3])[CH3:2].C=O.[C:16]([O:19][C:20](=O)C)(=[O:18])[CH3:17]>C(#N)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:1]([O:4][C:5]([C:7]1[N:8]([CH2:20][O:19][C:16](=[O:18])[CH3:17])[C:9]([Cl:13])=[C:10]([Cl:12])[N:11]=1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 7918Acetic AnhydrideHCID 54140329HCID 54140329, compound

Product 1

HCID 53742100HCID 53742100, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6342AcetonitrileSolvent

Procedure

44.6 g (0.2 mol) of 4,5-dichloro-imidazole-2-carboxylic acid isopropyl ester were stirred in 200 ml of acetonitrile together with 12 g (0.4 mol) of paraformaldehyde, 40.7 g (0.4 mol) of acetic anhydride and 0.5 g of p-toluenesulphonic acid for 20 hours at 85° C. After distilling off the solvent and stirring the residue in isopropanol, 38 g (64% of theory) of 1-acetoxymethyl-4,5-dichloro-imidazole-2-carboxylic acid isopropyl ester with a melting point of 81°-82° C. were obtained.

Workup

  1. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-2831535253b0452eabf052a446b7cb37
Source dataset
uspto-grants-1980_02
Patent number
US04187101

Reaction notes

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