4-Nitrophenol → HCID 178512722, compound

HRID 615913Notes

Reaction equation

HRID 615913 reaction equation
Cl.Cl.[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH2:16])[N:11]=1)[C:4]([NH2:6])=[NH:5].[C:17]1([S:23]([NH:26][C:27]2[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=2)[C:30](OC2C=CC([N+]([O-])=O)=CC=2)=[O:31])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(S(NC2C=C(C=CC=2)C(O)=O)(=O)=O)C=CC=CC=1.[N+](C1C=CC(O)=CC=1)([O-])=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[C:17]1([S:23]([NH:26][C:27]2[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=2)[C:30]([NH:16][CH2:15][CH2:14][S:13][CH2:12][C:10]2[N:11]=[C:7]([NH:3][C:4]([NH2:6])=[NH:5])[S:8][CH:9]=2)=[O:31])(=[O:24])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 7922013-Benzenesulfonamidobenzoic acidHCID 541944984-Nitrophenyl 3-[(benzenesulfonyl)amino]benzoateHCID 178478806HCID 178478806, compound

Product 1

HCID 178512722HCID 178512722, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5.5 g of 2-(2-guanidinothiazol-4-ylmethylthio)ethylamine dihydrochloride, 3.65 g of triethylamine and 3.7 g of 4-nitrophenyl 3-benzenesulfonamidobenzoate (m.p. 175°-178° C., prepared from 3-benzenesulfonamidobenzoic acid and 4-nitrophenol in methylene chloride in the presence of dicyclohexylcarbodiimide) is stirred at the temperature of 40° C. for 90 minutes, then it is evaporated under reduced pressure to dryness. The residue is taken up with 150 ml of ethyl acetate and washed twice with 10 ml of water. The solution is dried on anhydrous sodium sulfate, evaporated and the residue is chromatographied on silica with a chloroform:ethanol 4:1 mixture. Thus, 3.8 g of 3-benzenesulfonamido-N-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]benzamide are obtained as an oil which is dissolved in absolute ethanol and treated with fumaric acid in absolute ethanol. Thus, 3.6 g of crude product are obtained, which, after crystallization from 40 ml of 95% ethanol, gives 2.4 g of neutral fumarate of 3-benzenesulfonamido-N-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]benzamide, SR 57963 A, C20H22N6O3S4.1/2C4H4O4 ; m.p. 139°-141° C.

Workup

  1. customit is evaporated under reduced pressure to dryness
  2. washwashed twice with 10 ml of water
  3. dry with materialThe solution is dried on anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-73c76ef609a842048fecc2a250e80b2c
Source dataset
uspto-grants-1985_02
Patent number
US04501747

Reaction notes

Loading…