Sulfuryl chloride → HCID 14535763, compound

HRID 1904289Notes

Reaction equation

HRID 1904289 reaction equation
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[C:6]([NH:11][C:12](=[O:17])[CH2:13][C:14]([CH3:16])=O)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH2:19][C:20]([NH2:22])=[S:21].S(Cl)(Cl)(=O)=O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[C:6]([NH:11][C:12]([C:13]3[S:21][C:20]([NH2:22])=[N:19][C:14]=3[CH3:16])=[O:17])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 2723790ThioureaHCID 20038802N-(2,3-Dihydro-1,1-dimethyl-1H-inden-4-yl)-3-oxobutanamide

Product 1

HCID 14535763HCID 14535763, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1.00 g (4.08 mmol) of N-(1,1-dimethyl-4-indanyl)acetoacetamide and 0.62 g (8.16 mmol) of thiourea were dissolved in 10 ml of benzene and to this solution was added dropwise a solution of 0.55 g (4.08 mmol) of sulfuryl chloride in 5 ml of benzene at room temperature. After reacting for 2 hours at this temperature, the reaction mixture was refluxed for 1 hour, and left overnight. Then, the resulting solution was concentrated and dissolved in hot water and thereafter neutralyzed with 28% aqueous ammonia to give a precipitate. This precipitate was filtered, washed with water and dried to obtain 1.00 g of N-(1,1-dimethyl-4-indanyl)-2-amino-4-methylthiazole-5-carboxamide (yield 81%).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. waitleft overnight
  3. concentrationThen, the resulting solution was concentrated
  4. dissolutiondissolved in hot water
  5. customto give a precipitate
  6. filtrationThis precipitate was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-c36f7d9081b545fe98bfdf8c7d3ce7f3
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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