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

HRID 1904287Notes

Reaction equation

HRID 1904287 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.[Cl:19][C:20]1[S:21][C:22]([C:26](Cl)=[O:27])=[C:23]([CH3:25])[N:24]=1.O>O1CCCC1>[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[C:6]([NH:11][C:26]([C:22]3[S:21][C:20]([Cl:19])=[N:24][C:23]=3[CH3:25])=[O:27])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 131156151,1-Dimethyl-2,3-dihydro-1H-inden-4-amineHCID 135933932-Chloro-4-methylthiazole-5-carboxylic acid chloride

Product 1

HCID 14535761N-(1,1-dimethyl-4-indanyl)-2-chloro-4-methylthiazole-5-carboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.82 g (5.07 mmol) of 1,1-dimethyl-4-aminoindan and 0.48 g (6.08 mmol) of pyridine in 10 ml of tetrahydrofuran was added dropwise with stirring below 5° C. under ice cooling, a solution of 0.99 g (5.07 mmol) of 2-chloro-4-methylthiazole-5-carboxylic acid chloride in 3 ml of tetrahydrofuran, followed by stirring at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 5% hydrochloric acid and then water and was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain crystals, which was washed with n-hexane and dried to obtain 1.51 g of N-(1,1-dimethyl-4-indanyl)-2-chloro-4-methylthiazole-5-carboxamide (yeild 93%).

Workup

  1. stirringby stirring at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 5% hydrochloric acid
  4. dry with materialwater and was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain crystals, which
  7. washwas washed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-cbb78989544144cab9e54c73d9219a5f
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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