Hydrochloric Acid → HCID 21845587, compound

HRID 619027Notes

Reaction equation

HRID 619027 reaction equation
Br.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([NH2:21])[S:19][CH:20]=2)=[CH:12][C:11]=1[O:22][CH3:23])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:24]1(C)[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>N1C=CC=CC=1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([NH:21][S:30]([C:27]3[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=3)(=[O:32])=[O:31])[S:19][CH:20]=2)=[CH:12][C:11]=1[O:22][CH3:23])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 21845557HCID 21845557, compound

Product 1

HCID 21845587HCID 21845587, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(4-benzyloxy-3-methoxy-phenyl)-thiazol-2-ylamine hydrobromide with 0.27 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 chromatographed on 40 g of Kieselgel 60 with diethyl ether/hexane (2:1) as the eluent. Concentration of the product-containing fractions yielded 0.35 g of N-[4-(4-benzyloxy-3-methoxy-phenyl)-thiazol-2-yl]-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. customThe residue was chromatographed on 40 g of Kieselgel 60 with diethyl ether/hexane (2:1) as the eluent

Sources & evidence

ORD record
ord-a940c38ed9b74f2bb21f02c633df74c1
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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