Benzenesulfonamide → HCID 21566305, compound

HRID 1580326Notes

Reaction equation

HRID 1580326 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][CH:5]([NH:8][C:9](=S)[NH2:10])[CH2:4][CH2:3]1.C1(S(N)(=O)=[O:20])C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].N([O-])=O.[Na+]>O1CCOCC1.CC(C)=O.CC(C)=O.C(O)(=O)C>[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:20])[NH2:10])[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 64399499HCID 64399499, compound

Product 1

HCID 21566305HCID 21566305, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×HCID 22407776HCID 22407776, compoundSolvent

Procedure

2.9 g of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)- benzene-sulfonyl]-N'-(4.4-dimethylcyclohexyl)-thiourea (prepared by reaction of 4-[β-<2-methoxy-5-chlorobenzamido>-ethyl]-benzenesulfonamide with cyclohexyl mustard oil in dioxane/acetone in the presence of potassium carbonate) melting point 175°-177°C and decomposition, are dissolved in 250 ml acetone. An aqueous solution of 0.7 g sodium nitrite is added and while stirring is continued at 5°C, 15 ml of 5N acetic acid are added dropwise. After stirring for 21/2 hours acetone is distilled off. The residue is dissolved in dilute sodium hydroxide solution, the solution is clarified with charcoal and acidified. There is obtained a crystalline precipitate of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(4.4-dimethylcyclohexyl)-urea, which is filtered off with suction and recrystallized from dilute methanol. The substance melts at 174°-176°C. 2. (a) 5.38 g of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)benzene-sulfonyl]-N'-(4.4-dimethylcyclohexyl)-thiourea are dissolved in 5 ml dioxane and 250 ml methanol. Then 2.16 g of mercury peroxide are added and stirring is continued for 4 hours at 60°C. The mercury sulfide formed is filtered off, and the filtrate is half concentrated and water is added. After abandoning during the night a crystalline precipitate has formed, which is filtered off with suction and recrystallized from dilute methanol. The N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(4.4-dimethylcyclohexyl)-isoureamethylether thus obtained melts at 149°-151°C.

Workup

  1. customis continued at 5°C
  2. distillationis distilled off
  3. dissolutionThe residue is dissolved in dilute sodium hydroxide solution

Sources & evidence

ORD record
ord-47db9ad6afd24392b09e47db1fc5be0b
Source dataset
uspto-grants-1976_01
Patent number
US03932503

Reaction notes

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