2-Chlorobenzoyl chloride → HCID 178512325, compound

HRID 66584Notes

Reaction equation

HRID 66584 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]([NH:22][C:23]#[N:24])=[N:18][CH2:19][CH2:20][NH2:21])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39]>CO.CCOCC>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39].[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]([NH:22][C:23]#[N:24])=[N:18][CH2:19][CH2:20][NH:21][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=3[Cl:25])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 444266Maleic AcidHCID 178512326HCID 178512326, compound

Product 1

HCID 178512325HCID 178512325, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-guanidino-4-{3-[3-cyano-2-(2-aminoethyl)guanidino]cyclohexyl}thiazole (0.5 g.) in methanol (30 ml.) was added o-chlorobenzoyl chloride (0.4 g.) and the mixture allowed to stand at room temperature for 16 hours. The residue obtained by evaporation of the solvent was partitioned between ethyl acetate (100 ml.) and water (20 ml.) The organic layer was isolated, washed with water (20 ml), dried (magnesium sulphate) and evaporated. The residue was subjected to preparative thin layer chromatography on Merck 60 F-254 plates using chloroform/methanol/aqueous ammonia (s.g. 0.88) 80:20:0.1 v/v/v for development. The appropriate zone of the chromatogram was isolated and extracted with hot ethanol/chloroform 50:50 v/v (200 ml.) and the residue obtained on evaporation of the solvents was dissolved in methanol. To this solution was added an excess of maleic acid in ether followed by a further amount of ether until precipitation began. The white powder precipitate (0.2 g.) was washed with ether to give 2-guanidino-4-{ 3-[3-cyano-2-(2-(2-chlorobenzoylamino)ethyl)guanidino]cyclohexyl}thiazole hydrogen maleate, m.p. 158°-165° (decomp.).

Workup

  1. customThe residue obtained by evaporation of the solvent
  2. customwas partitioned between ethyl acetate (100 ml.) and water (20 ml.) The organic layer
  3. customwas isolated
  4. washwashed with water (20 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customThe appropriate zone of the chromatogram was isolated
  8. extractionextracted with hot ethanol/chloroform 50:50 v/v (200 ml.)
  9. customthe residue obtained on evaporation of the solvents
  10. customfollowed by a further amount of ether until precipitation
  11. washThe white powder precipitate (0.2 g.) was washed with ether

Sources & evidence

ORD record
ord-1b8fe65dc4fe4f8abfe947e48e2116da
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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