Hydrochloric Acid → HCID 9841436, compound

HRID 1598631Notes

Reaction equation

HRID 1598631 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:8][C:4]=1[C:5](Cl)=[O:6])[CH3:2].[NH2:22][C:23]([NH2:25])=[NH:24].Cl>COCCOC>[NH2:24][C:23]([NH2:25])=[N:22][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([S:18]([CH3:21])(=[O:20])=[O:19])[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:11][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3520GuanidineHCID 18930097HCID 18930097, compound

Product 1

HCID 9841436HCID 9841436, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

6.6 g of 2-ethyl-4-piperidino-5-methylsulfonylbenzoyl chloride [obtainable by reacting 2-ethyl-4-chloro-5-methylsulfonylbenzoic acid with excess piperidine followed by chlorination with SOCl2 ] dissolved in 60 ml of ethylene glycol dimethyl ether are added dropwise to a solution of 8.7 g of guanidine in 60 ml of ethylene glycol dimethyl ether, and the mixture is stirred at 25° for one hour. 200 ml of ice-water are then added to the reaction mixture, which is acidified with 1N HCl, and subjected twice to extraction with 100 ml of ethyl acetate each time, and the organic phase is discarded. The aqueous phase is rendered alkaline with 1N NaOH and cooled. The product which precipitates is filtered off with suction to give N-diaminomethylene-2-ethyl-4-piperidino-5-methylsulfonylbenzamide, m.p. 218°-220°.

Workup

  1. extractionsubjected twice to extraction with 100 ml of ethyl acetate each time
  2. temperaturecooled
  3. customThe product which precipitates
  4. filtrationis filtered off with suction

Sources & evidence

ORD record
ord-96772a8d931c4d979a936359dfa131a2
Source dataset
uspto-grants-1998_04
Patent number
US05739142

Reaction notes

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