Ethyl Acetate → 4-methyl-N-(1,1,3-trimethylindan-4-yl)-1,2,3-thiadiazole-5-carboxamide

HRID 1031938Notes

Reaction equation

HRID 1031938 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.C(OCC)(=O)C.[NH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]([CH3:32])[CH2:24][C:25]2([CH3:31])[CH3:30]>N1C=CC=CC=1.C(N(CC)CC)C>[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[C:7]([NH:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]([CH3:32])[CH2:24][C:25]2([CH3:31])[CH3:30])=[O:9]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acidHCID 112175411,1,3-Trimethylindan-4-amine

Product 1

HCID 146987854-methyl-N-(1,1,3-trimethylindan-4-yl)-1,2,3-thiadiazole-5-carboxamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 1.5 g (10.4 mmols) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 5 ml of thionyl chloride, and one drop of pyridine was refluxed for 1 hour. The resultant solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was dissolved in 10 ml of ethyl acetate. This solution was added to 10 ml of ethyl acetate solution of 1.7 g (9.7 mmols) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine, and the resultant solution was stirred at room temperature for 3 hours. The resultant reaction solution was sequentially washed with water, aqueous sodium hydrogen carbonate solution, water, and a saturated brine, and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/9), to obtain 2.17 g of white crystals (Compound No. 14 shown in Table 6). The yield was 69.1%.

Workup

  1. temperaturewas refluxed for 1 hour
  2. distillationThe resultant solution was distilled under reduced pressure
  3. customto remove excess thionyl chloride
  4. dissolutionThe obtained residue was dissolved in 10 ml of ethyl acetate
  5. customThe resultant reaction solution
  6. washwas sequentially washed with water, aqueous sodium hydrogen carbonate solution, water
  7. concentrationa saturated brine, and then concentrated under reduced pressure
  8. customThe concentrated residue was separated
  9. custompurified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/9)

Sources & evidence

ORD record
ord-7b7c7102205a40b29e30ec4b90096fdf
Source dataset
uspto-grants-1990_09
Patent number
US04956375

Reaction notes

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