HCID 9837522, compound → HCID 10522547, compound

HRID 1417246Notes

Reaction equation

HRID 1417246 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]([NH2:13])=[S:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)=O>C(O)C>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:13]=[C:11]([NH:10][S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:14])=[CH:6][CH:5]=3)(=[O:9])=[O:8])[S:12][CH:16]=2)=[CH:20][C:21]=1[CH3:26]

Participants

4

Reactant 2

HCID 9837522HCID 9837522, compoundHCID 112184492-Bromo-1-(4-hydroxy-3-methylphenyl)ethanone

Product 1

HCID 10522547HCID 10522547, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 26 g of 4-toluenesulfonyl-thiourea in 225 ml of ethanol was treated with 25.9 g of 2-bromo-1-(4-hydroxy-3-methyl-phenyl)-ethanone, left to stand at room temperature for 3 days and then boiled for a brief period. The reaction mixture was evaporated to dryness in a vacuum and subsequently partitioned between water and ethyl acetate. The aqueous phase was extracted once with ethyl acetate, the organic phases were combined, dried with sodium sulphate and concentrated. The residue was chromatographed on 500 g of Kieselgel 60 with ethyl acetate/hexane (1:1) as the eluent. The product-containing fractions were concentrated and, after recrystallization from 50% ethanol, yielded 10.1 g of N-[4-(4-hydroxy-3-methyl-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as colourless crystals.

Workup

  1. waitleft
  2. waitboiled for a brief period
  3. customThe reaction mixture was evaporated to dryness in a vacuum
  4. customsubsequently partitioned between water and ethyl acetate
  5. extractionThe aqueous phase was extracted once with ethyl acetate
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on 500 g of Kieselgel 60 with ethyl acetate/hexane (1:1) as the eluent
  9. concentrationThe product-containing fractions were concentrated
  10. customafter recrystallization from 50% ethanol

Sources & evidence

ORD record
ord-0dc488b3c19f40af812c3560a206ebca
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Reaction notes

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