Benzenesulfonamide → HCID 22105582, compound

HRID 1455940

Reaction equation

HRID 1455940 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 22105582HCID 22105582, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-598886c70a264870925ddd16e07dd090
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Linked notes

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