Ammonia → 6-[m-(1,3-Dimethylpyrazole-5-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

HRID 2166817Notes

Reaction equation

HRID 2166817 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][N:14]3[C:10]([S:11][CH2:12][CH2:13]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C[Al](C)C.C([O:22][C:23]([C:25]1[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=1)=O)C.Cl.N>ClCCl>[CH3:30][N:29]1[C:25]([C:23]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]3[CH2:15][N:14]4[C:10]([S:11][CH2:12][CH2:13]4)=[N:9]3)[CH:5]=[CH:6][CH:7]=2)=[O:22])=[CH:26][C:27]([CH3:31])=[N:28]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1385761,3-Dimethyl-5-ethoxycarbonylpyrazoleHCID 30386693-AminolevamisoleHCID 16682925Trimethylaluminum

Product 1

HCID 204979636-[m-(1,3-Dimethylpyrazole-5-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazoleYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (2.4 g, 11 mmol) in dry dichloromethane (30 ml) under nitrogen was added trimethylaluminium (4.8 ml; 25% in hexane). After 20 mins at room temperature 1,3-dimethylpyrazole-5-carboxylic acid ethyl ester (1.8 g, 11 mmol) in dry dichloromethane (1 ml) was added and the mixture heated under reflux for 24 hours. Hydrochloric acid (20 ml; 2 N aqueous) was added slowly, the resulting mixture basified with aqueous ammonia solution (5 N; 100 ml) and extracted with chloroform (3×200 ml) which after drying (MgSO4) and concentrating in vacuo afforded an oil. Separation of the oil on alumina eluting with chloroform gave the amide (1.28 g; 34%).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with chloroform (3×200 ml) which
  4. dry with materialafter drying (MgSO4)
  5. concentrationconcentrating in vacuo
  6. customafforded an oil
  7. customSeparation of the oil on alumina eluting with chloroform

Sources & evidence

ORD record
ord-9929c6169ddc447588ffb1f896987a90
Source dataset
uspto-grants-1983_06
Patent number
US04389406

Reaction notes

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