Thiourea → Methyl 2-amino-4-(4-methoxyphenyl)thiazole-5-carboxylate

HRID 2186205Notes

Reaction equation

HRID 2186205 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1OC)=O.[OH:16][C:17]1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1.[NH2:35][C:36]([NH2:38])=[S:37]>C(#N)C>[NH2:35][C:36]1[S:37][C:4]([C:3]([O:2][CH3:1])=[O:15])=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[N:38]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 2759697Methyl 3-(2-methoxyphenyl)-3-oxopropanoateHCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 18177280Methyl 2-amino-4-(4-methoxyphenyl)thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl-3-(methoxyphenyl)-3-oxopropionate (33.34 g, 95.75 mmol) and hydroxy(tosyloxy)Iodobenzene (37.55 g, 95.75 mmol) were combined in 350 mL of acetonitrile and refluxed for 45 min. followed by the addition of thiourea (7.29 g, 95.75 mmol) and refluxed for 2 h. The volatiles were removed in vacuum and the residue dissolved in 50/50 EtOAc/Hexane and passed through a plug of silica gel. Once the impurities eluted, the product was recovered by eluting with 100% EtOAC and removing the volatiles in vacuum. The title compound was obtained as a tan solid (38.52 g, 75%) MS (NH3-DCI) 254.2 (M+H)+.

Workup

  1. temperaturerefluxed for 45 min.
  2. temperaturerefluxed for 2 h
  3. customThe volatiles were removed in vacuum
  4. dissolutionthe residue dissolved in 50/50 EtOAc/Hexane
  5. washOnce the impurities eluted
  6. customthe product was recovered
  7. washby eluting with 100% EtOAC
  8. customremoving the volatiles in vacuum

Sources & evidence

ORD record
ord-bcf835126cd147fe80603d918c1894a6
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

Loading…