Hydrochloric Acid → HCID 21845560, compound

HRID 1417247Notes

Reaction equation

HRID 1417247 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[N:6]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1>[C:10]([C:9]1[CH:8]=[C:7]([C:5]2[N:6]=[C:2]([NH:1][S:21]([C:18]3[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[S:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=1)#[N:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 27565583-(2-Amino-thiazol-4-yl)-benzonitrile

Product 1

HCID 21845560HCID 21845560, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 3-(2-amino-thiazol-4-yl)-benzonitrile with 0.52 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 50 ml of 1N hydrochloric acid and the solid which thereby separated was filtered off and dissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.4 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 80 ml of 50% ethanol yielded 0.35 g of N-[4-(3-cyano-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as colorless crystals.

Workup

  1. customthe solid which thereby separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 0.4 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. customThe product separated upon neutralization with concentrated hydrochloric acid
  7. customRecrystallization from 80 ml of 50% ethanol

Sources & evidence

ORD record
ord-497bdb8f4a7e497fafd6356c5878034a
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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