Hydrochloric Acid → 1H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-

HRID 2292828Notes

Reaction equation

HRID 2292828 reaction equation
[Cl:1][C:2]1[NH:6][C:5]([CH2:7][CH2:8][CH3:9])=[N:4][CH:3]=1.[CH3:10][O:11]C(N(C)C)OC.C(N(CC)CC)C.Cl.[OH-].[Na+]>ClC1C=CC=CC=1>[CH2:7]([C:5]1[NH:6][C:2]([Cl:1])=[C:3]([CH:10]=[O:11])[N:4]=1)[CH2:8][CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 21466603HCID 21466603, compound

Product 1

HCID 97939751H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 5-chloro-2-propyl-1H-imidazole (1.45 g, 10 mmol), dimethoxymethyldimethylamine (1.55 g. approximately 92 percent pure, 12 mmol) and triethylamine (0.10 g, 1 mmol) in chlorobenzene (50 ml) was heated for 1 hour at 80% and 2.5 hours under reflux, cooled to room temperature and poured into 2M hydrochloric acid (100 ml). The pH was adjusted to pH 1.97 by addition of 30 percent strength sodium hydroxide solution (19 ml) and the mixture was extracted three times, each time with 50 ml of ethyl acetate. The combined organic phases were dried and concentrated on a rotavapor. The yield of the product was 1.27 g (approximately 90 percent pure according to H-NMR), 66 percent based on 5-chloro-2-propyl-1H-imidazole. Other data concerning the product was:

Workup

  1. temperatureunder reflux
  2. extractionthe mixture was extracted three times
  3. customThe combined organic phases were dried
  4. concentrationconcentrated on a rotavapor

Sources & evidence

ORD record
ord-a05b149d9b974d9c941b2a1d399aa19c
Source dataset
uspto-grants-1997_11
Patent number
US05684157

Reaction notes

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