Guanidine → HCID 18927266, compound

HRID 1600433Notes

Reaction equation

HRID 1600433 reaction equation
[NH2:1][C:2]([NH2:18])=[N:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8](Cl)=[CH:7][C:6]=1[CH3:16].C[C:20]1[CH:28]=[C:27](Cl)[C:26]([S:30](C)(=O)=O)=[CH:25][C:21]=1C(Cl)=O.N[C:35](N)=N.C1(S)C=CC=CC=1>O.C(N(CC)CC)C>[NH2:1][C:2]([NH2:18])=[N:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([S:30][C:26]2[CH:25]=[CH:21][CH:20]=[CH:28][C:27]=2[CH3:35])=[CH:7][C:6]=1[CH3:16]

Participants

7

Reactant 4

HCID 3520GuanidineHCID 7969ThiophenolHCID 10517570HCID 10517570, compoundHCID 18927300HCID 18927300, compound

Product 1

HCID 18927266HCID 18927266, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 1 g of N-diaminomethylene-2-methyl-4-chloro-5-methylsulfonylbenzamide [obtainableby reaction of 2-methyl-4-chloro-5-methylsulfonylbenzoyl chloride with guanidine in the presence of triethylamine], 7 ml of thiophenol and 6 g ofK2CO3 is heated at 180° for 90 min. It is dissolved in water and extracted with ethyl acetate, and the extract is evaporated. N-Diaminomethylene-2-methyl-4-(2-methylphenylthio)-5-methylsulfonylbenzamide is obtained, from which, after treatment with 1.5 g of sodium perborate in 30 ml of glacial acetic acid over a period of 2 hours at 60° C. in a water bath, N-diaminomethylene-2-methyl-4-(2-methylphenylsulfonyl)-5methylsulfonylbenzamide is obtained after customary working up.

Workup

  1. temperatureis heated at 180° for 90 min
  2. extractionextracted with ethyl acetate
  3. customthe extract is evaporated

Sources & evidence

ORD record
ord-a9bae023ce4947098dd08585511b340e
Source dataset
uspto-grants-1998_04
Patent number
US05744641

Reaction notes

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