3-Pyridinemethanamine → 4-[4-Chloro-3-(3-picolylsulfamoyl)-phenyl]-3-methyl-2-methylimino-1,3-thiazolidine-4-ol

HRID 461190Notes

Reaction equation

HRID 461190 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:17])[CH2:13][S:12][C:11](=[N:14][CH3:15])[N:10]2[CH3:16])=[CH:5][C:4]=1[S:18](Cl)(=[O:20])=[O:19].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH2:29])[CH:23]=1>C(N(CC)CC)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:17])[CH2:13][S:12][C:11](=[N:14][CH3:15])[N:10]2[CH3:16])=[CH:5][C:4]=1[S:18](=[O:20])(=[O:19])[NH:29][CH2:28][C:24]1[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 227604894-Chloro-3-chlorosulfonylphenyl-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide

Product 1

HCID 227606964-[4-Chloro-3-(3-picolylsulfamoyl)-phenyl]-3-methyl-2-methylimino-1,3-thiazolidine-4-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

8.8 g of 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide were reacted with 3.0 g of 3-picolyl amine and 5 g of triethyl amine according to Example 76, the solvent was distilled off under reduced pressure and the residue was taken up in 70 ml of water. Three extractions followed with 60 ml of ethyl acetate, the organic phase was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue crystallized under diisopropyl ether. Melting point: 152° - 153° C.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThree extractions
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue crystallized under diisopropyl ether

Sources & evidence

ORD record
ord-86948021a7bb48a599e8f28e04833188
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

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