Benzenesulfonamide → HCID 22105582, 화합물

HRID 1455940

반응식

HRID 1455940 반응식
Cl.CN(C)CCCC(N=C=N)C.[CH2:13]([O:20][C:21]1[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][C:22]=1[CH2:23][N:24]([C:27]1[S:28][C:29]([C:32]([OH:34])=O)=[CH:30][N:31]=1)[CH2:25][CH3:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:40]1([S:46]([NH2:49])(=[O:48])=[O:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O.O>[CH2:13]([O:20][C:21]1[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][C:22]=1[CH2:23][N:24]([C:27]1[S:28][C:29]([C:32]([NH:49][S:46]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:48])=[O:47])=[O:34])=[CH:30][N:31]=1)[CH2:25][CH3:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

8

반응물 4

HCID 7370BenzenesulfonamideHCID 8471TriethylamineHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 22105530HCID 22105530, 화합물

생성물 1

HCID 22105582HCID 22105582, 화합물

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

1-(3--Dimethylaminopropyl)ethylcarbodiimide hydrochloride (0.85 g) was added to a stirred mixture of 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]thiazole-5-carboxylic acid (1 g), benzenesulphonamide (0.35 g), 4-dimethylaminopyridine (0.27 g) and triethylamine (0.225 g) in N,N-dimethylformamide (100 mL) and the mixture was stirred at ambient temperature for 16 hours. Water (30 mL) was added to the reaction mixture which was then extracted three times with ethyl acetate (20 mL each time). The combined ethyl acetate extracts were washed consecutively with aqueous 2N HCL (3×10 mL), aqueous saturated NaHCO solution (3×10 mL) and water (10 mL) and dried. The residue obtained on evaporation of the solvent was filtered through silica using ethyl acetate as eluant. The solvent was evaporated and on trituration with diethyl ether the residue gave 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]-N-(phenylsulphonyl)thiazole-5-carboxamide, yield 0.358 g, mp 140°-145° C.

후처리

  1. extractionwas then extracted three times with ethyl acetate (20 mL each time)
  2. washThe combined ethyl acetate extracts were washed consecutively with aqueous 2N HCL (3×10 mL), aqueous saturated NaHCO solution (3×10 mL) and water (10 mL)
  3. customdried
  4. customThe residue obtained on evaporation of the solvent
  5. filtrationwas filtered through silica
  6. customThe solvent was evaporated and on trituration with diethyl ether the residue

출처 및 근거

ORD 기록
ord-598886c70a264870925ddd16e07dd090
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843942

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