Benzenesulfonamide → HCID 22105582、化合物

HRID 1455940

反応式

HRID 1455940 の反応式
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

参加物

8

反応物 4

HCID 7370BenzenesulfonamideHCID 8471TriethylamineHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 22105530HCID 22105530、化合物

生成物 1

HCID 22105582HCID 22105582、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-598886c70a264870925ddd16e07dd090
出典データセット
uspto-grants-1998_12
特許番号
US05843942

関連ノート

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