Hydrochloric Acid → Hydrochloric Acid

HRID 1598633Notes

Reaction equation

HRID 1598633 reaction equation
[CH3:1][C:2]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:3]=1[C:4](OC)=[O:5].[NH2:22][C:23]([NH2:25])=[NH:24].[ClH:26].C[O-].[Na+]>CO.O>[NH2:24][C:23]([NH2:25])=[N:22][C:4](=[O:5])[C:3]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:2]=1[CH3:1].[ClH:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3520GuanidineHCID 10686489HCID 10686489, compoundHCID 10942334Sodium Methoxide

Product 2

HCID 313Hydrochloric AcidHCID 10688406HCID 10688406, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 20 g of methyl 2-methyl-4-piperidino-5-methylsulfonylbenzoate [obtainable by reacting piperidine with 2-methyl-4-chloro-5-methylsulfonylbenzoic acid followed by esterification] and 30 g of guanidine, which has been liberated beforehand from the guanadine hydrochloride using sodium methylate, is stirred in 160 ml of methanol at 50° over a period of twenty hours. After cooling to 0°, water is added, stirring is continued for 1 hour and the precipitate which forms is separated off. Recrystallization from dichloromethane/methanol gives N-diaminomethylene-2-methyl-4-piperidino-5-methylsulfonylbenzamide, m.p. 222°-224°, hydrochloride m.p. 275°-276°.

Workup

  1. temperatureAfter cooling to 0°
  2. customthe precipitate which forms is separated off
  3. customRecrystallization from dichloromethane/methanol

Sources & evidence

ORD record
ord-a529a226f4934297933aaad4d58b8cdf
Source dataset
uspto-grants-1998_04
Patent number
US05739142

Reaction notes

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