Hydrochloric Acid → HCID 19965158, compound

HRID 977100Notes

Reaction equation

HRID 977100 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([OH:18])[C:14]([CH3:17])([CH3:16])[CH3:15].[H-].[Na+].Cl>CN(C)C=O>[CH2:13]([O:18][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6404Neopentyl alcoholHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 24758Sodium hydride

Product 1

HCID 19965158HCID 19965158, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.83 g of 4-Chloro-3-nitrobenzonitrile and 1.06 g of neopentyl alcohol were dissolved in 10 ml of N,N-dimethylformamide. The solution was cooled to 0° C., and 480 mg of sodium hydride (60% in oil) was gradually added thereto. Then, 30 min after the addition, 13 ml of 1N hydrochloric acid was added to the mixture, and the precipitated crystal was collected by filtration to give 2.12 g of 4-neopentyloxy-3-nitrobenzonitrile. 1.2 g of thioacetamide was added thereto, and the mixture was heated at 80° C. for an hour in N,N-dimethylformamide saturated with hydrochloric acid. After the completion of the reaction, the reaction mixture was neutralized with 30 ml of water and 18 ml of 2N sodium hydroxide, and the lower layer was separated and dried. The lower layer was dissolved in 30 ml of ethanol, 2.11 g of ethyl 2-chloroacetoacetate was added thereto, and the mixture was heated under reflux for 5 hours. After the reaction mixture was cooled, the precipitated crystal was collected by filtration and recrystallized from ethanol to give 2.38 g of ethyl 4-methyl-2-(4-neopentyloxy-3-nitrophenyl)-5-thiazolecarboxylate (yield: 63%). This product was hydrolyzed by a conventional process, and the resulting crystal was recrystallized from a 80% aqueous ethanol solution to give 1.98 g of 2-(4-neopentyloxy-3-nitrophenyl)-4-methyl-5-thiazolecarboxylic acid (yield:

Workup

  1. additionwas added to the mixture
  2. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-c9846c28ac21454cad25d98e4f914c32
Source dataset
uspto-grants-1997_03
Patent number
US05614520

Reaction notes

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