Hydrochloric Acid → 2-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole

HRID 1531398Notes

Reaction equation

HRID 1531398 reaction equation
C[O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:4]=1[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1)=[O:6].C(NCCCC)CCC.Cl.O>CN(C)C(=O)C>[CH3:23][O:22][C:20]1[C:19]([O:24][CH3:25])=[CH:18][C:4]([C:5]([NH:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=2)=[O:6])=[C:3]([OH:2])[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8148DibutylamineHCID 10215672Ethyl 2-(2,4,5-trimethoxybenzamido)thiazole-4-carboxylate

Product 1

HCID 155080092-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazoleYield 92.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A suspension (30 ml) of 2-[N-(2,4,5-trimethoxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole (10.0 g) in N,N-dimethylacetamide was allowed to dissolve with heat at a temperature of at least 150° C., and di-n-butylamine (8.8 g) was added dropwise to the solution, refluxed for 5 hours. The reaction mixture was allowed to cool, poured into a mixture of 1 N hydrochloric acid (100 ml) and ice water (100 ml), and further, water was added thereto. The crystals so precipitated were collected by filtration, washed with water, and then subjected to air drying and drying under reduced pressure to thereby obtain crude crystals (10.0 g). The crystals were followed by recrystallization from 1,4-dioxane, thereby 8.9 g of 2-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole was obtained (yield: 82.3%).

Workup

  1. dissolutionto dissolve
  2. additionwas added dropwise to the solution
  3. temperaturerefluxed for 5 hours
  4. temperatureto cool
  5. customThe crystals so precipitated
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdrying
  9. customdrying under reduced pressure
  10. customto thereby obtain crude crystals (10.0 g)
  11. customThe crystals were followed by recrystallization from 1,4-dioxane

Sources & evidence

ORD record
ord-6c73e7815477408e8e0e51901b28fe38
Source dataset
uspto-grants-2001_03
Patent number
US06197970B1

Reaction notes

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