4-Nitrophenol → HCID 178505019, compound

HRID 615912Notes

Reaction equation

HRID 615912 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:15][S:16]([NH:19][C:20]1[CH:21]=[C:22]([CH:35]=[CH:36][CH:37]=1)[C:23](OC1C=CC([N+]([O-])=O)=CC=1)=[O:24])(=[O:18])=[O:17].CS(NC1C=C(C=CC=1)C(O)=O)(=O)=O.[N+](C1C=CC(O)=CC=1)([O-])=O.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.C(Cl)[Cl:85]>CO>[ClH:85].[CH3:15][S:16]([NH:19][C:20]1[CH:21]=[C:22]([CH:35]=[CH:36][CH:37]=1)[C:23]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)=[O:24])(=[O:18])=[O:17]

Participants

9

Reactant 7

HCID 9804-NitrophenolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2257723-(Methylsulfonamido)benzoic AcidHCID 132595114-Nitrophenyl 3-[(methanesulfonyl)amino]benzoateHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178505019HCID 178505019, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 0.015 mol of 2-(2-guanidinothiazol-4-ylmethylthio)ethylamine, 0.015 mol of 4-nitrophenyl 3-methanesulfonamidobenzoate (m.p. 162°-164° C., prepared from 3-methanesulfonamidobenzoic acid and 4-nitrophenol in methylene chloride in the presence of dicyclohexylcarbodiimide) and 0.035 mol of triethylamine in 150 ml of methanol is heated at 40° C. under stirring for 4 hours. Then the solvent is evaporated under reduced pressure and the residue is taken up with 20 ml of water and 100 ml of ethyl acetate. The organic phase is dried on anhydrous sodium sulfate, the solvent is evaporated under reduced pressure and the residue is dissolved in 50 ml of warm ethyl acetate. The solution is filtered and the filtrate is acidified with hydrogen chloride in isopropanol. Thus, 3-methanesulfonamido-N-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]benzamide hydrochloride is obtained, which, after crystallization from 20 ml of water gives 2 g of the monohydrate, SR 57938 A; m.p. 117°-120° C.

Workup

  1. customThen the solvent is evaporated under reduced pressure
  2. dry with materialThe organic phase is dried on anhydrous sodium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. dissolutionthe residue is dissolved in 50 ml of warm ethyl acetate
  5. filtrationThe solution is filtered

Sources & evidence

ORD record
ord-825dc166a195438aadfb6e09e73465d0
Source dataset
uspto-grants-1985_02
Patent number
US04501747

Reaction notes

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