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Potassium Carbonate → N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide

HRID 1417302
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HRID 1417302 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:13]([CH2:24][O:25][CH3:26])[S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[Li+].[C:29]1(OB(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:2]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[N:9]=[C:10]([N:13]([CH2:24][O:25][CH3:26])[S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[S:11][CH:12]=2)[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 433294Lithium ChlorideHCID 21845556N-[4-(3-bromo-phenyl)-thiazol-2-yl]-N-methoxymethyl-4-methyl-benzenesulfonamide

생성물 1

HCID 21845572N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 962Water용매
HCID 1140Toluene용매

실험 절차

A solution of 0.5 g of N-[4-(3-bromo-phenyl)-thiazol-2-yl]-N-methoxymethyl-4-methyl-benzenesulfonamide in 8 ml of toluene was treated in succession with 0.1 g of anhydrous lithium chloride, 60 mg of tetrakis(triphenylphosphine)-palladium, 0.23 g of phenylboric acid and 2 ml of 2N potassium carbonate solution. The mixture was boiled overnight, cooled and, after the addition of water, extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulphate and concentrated. The residue was chromatographed on 80 g of Kieselgel 60 with ethyl acetate/hexane (1:4) as the eluent. The product-containing fractions were concentrated and yielded 0.29 g of colorless, amorphous N-(4-biphenyl-3-yl-thiazol-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide, which was processed without further purification.

후처리

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on 80 g of Kieselgel 60 with ethyl acetate/hexane (1:4) as the eluent
  6. concentrationThe product-containing fractions were concentrated

출처 및 근거

ORD 기록
ord-66c742d652e84359a5c1dd712800fb2d
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05877193

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