Water → N-(1,1,3-trimethyl-4-indanyl)-2-chloro-4-methylthiazole-5-carboxamide

HRID 1904288Notes

Reaction equation

HRID 1904288 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.[CH3:11][C:12]1([CH3:23])[C:20]2[C:15](=[C:16]([NH2:21])[CH:17]=[CH:18][CH:19]=2)[CH:14]([CH3:22])[CH2:13]1.O>C(Cl)Cl>[CH3:11][C:12]1([CH3:23])[C:20]2[C:15](=[C:16]([NH:21][C:8]([C:4]3[S:3][C:2]([Cl:1])=[N:6][C:5]=3[CH3:7])=[O:10])[CH:17]=[CH:18][CH:19]=2)[CH:14]([CH3:22])[CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 6669602-Chloro-4-methyl-1,3-thiazole-5-carboxylic acidHCID 112175411,1,3-Trimethylindan-4-amine

Product 1

HCID 14535768N-(1,1,3-trimethyl-4-indanyl)-2-chloro-4-methylthiazole-5-carboxamideYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

252 mg (1.42 mmol) of 2-chloro-4-methylthiazole-5-carboxylic acid and 442 mg (1.42 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidomethiodide were dissolved in 10 ml of methylene chloride and stirred at room temperature for 1 hour. Then, to the solution was added 249 mg (1.42 mmol) of 1,1,3-trimethyl-4-aminoindan and reaction was effected for 6 hours under reflux. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was concentrated and thereafter was purified by column chromatography (eluent; n-hexane:ethyl acetate=50:50 V/V) to obtain 204 mg of N-(1,1,3-trimethyl-4-indanyl)-2-chloro-4-methylthiazole-5-carboxamide (yield 43%).

Workup

  1. additionThen, to the solution was added
  2. waitwas effected for 6 hours
  3. temperatureunder reflux
  4. extractionextracted with methylene chloride
  5. concentrationThe organic layer was concentrated
  6. customwas purified by column chromatography (eluent; n-hexane:ethyl acetate=50:50 V/V)

Sources & evidence

ORD record
ord-935a7dab9601420ab3629bc3d7fc8dce
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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