Hydrochloric Acid → HCID 21845582, compound

HRID 1417250Notes

Reaction equation

HRID 1417250 reaction equation
Br.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:24]2[N:25]=[C:26]([NH2:29])[S:27][CH:28]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.Cl>N1C=CC=CC=1>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:24]2[N:25]=[C:26]([NH:29][S:36]([C:33]3[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=3)(=[O:38])=[O:37])[S:27][CH:28]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 21845568HCID 21845568, compound

Product 1

HCID 21845582HCID 21845582, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3,4-bis-benzyloxy-phenyl)-thiazol-2-ylamine hydrobromide with 0.23 g of p-toluenesulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored solution was poured into 50 ml of 1N hydrochloric acid and extracted three times with 50 ml of methylene chloride each time. The organic extracts were combined, dried with magnesium sulphate and concentrated. The residue was dissolved in a mixture of 20 ml of ethanol and 15 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 50 ml of 60% ethanol yielded 0.33 g of N-[4-(3,4-bis-benzyloxy-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as colorless crystals.

Workup

  1. extractionextracted three times with 50 ml of methylene chloride each time
  2. dry with materialdried with magnesium sulphate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of 20 ml of ethanol and 15 ml of 2N sodium hydroxide solution
  5. additionAfter the addition of 0.4 g of active charcoal the mixture
  6. filtrationsubsequently the active charcoal was filtered off
  7. customThe product separated upon neutralization with concentrated hydrochloric acid
  8. customRecrystallization from 50 ml of 60% ethanol

Sources & evidence

ORD record
ord-05723a3d9db749cfaf311ee140cb0132
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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