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

HRID 1531399Notes

Reaction equation

HRID 1531399 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].CNCCCCCC.Cl.O>CS(C)=O>[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 37079N-MethylhexylamineHCID 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 72.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension (6 ml) of 2-[N-(2,4,5-trimethoxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole (3.0 g) in dimethyl sulfoxide was dissolved with heat, and N-methyl-N-hexylamine (2.3 g) was added dropwise to the solution, refluxed for 2 hours. The reaction mixture was allowed to cool, poured into a mixture of 1 N hydrochloric acid (30 ml) and ice water (30 ml), and further, water was added thereto. Crystals so precipitated were collected by filtration, washed with water, and air-dried to thereby obtain crude crystals. The crystals were followed by recrystallization from 1,4-dioxane, 2.1 g of 2-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole was obtained (yield: 64.6%).

Workup

  1. temperaturewith heat
  2. temperaturerefluxed for 2 hours
  3. temperatureto cool
  4. customCrystals so precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customair-dried
  8. customto thereby obtain crude crystals
  9. customThe crystals were followed by recrystallization from 1,4-dioxane

Sources & evidence

ORD record
ord-31b492672ea540368d130ac4250fec95
Source dataset
uspto-grants-2001_03
Patent number
US06197970B1

Reaction notes

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