2-Piperidino-4-imino-2-thiazoline hydrochloride → HCID 178479152, compound

HRID 1112534Notes

Reaction equation

HRID 1112534 reaction equation
[ClH:1].[N:2]1([C:8]2[S:9][CH2:10][C:11](=[NH:13])[N:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[NH:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=N)[NH:16]1>CO>[ClH:1].[NH:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[C:10]2[S:9][C:8]([N:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)=[N:12][C:11]2=[NH:13])[NH:16]1

Participants

4

Reactant 2

HCID 162452962-Piperidino-4-imino-2-thiazoline hydrochlorideHCID 178508669HCID 178508669, compound

Product 1

HCID 178479152HCID 178479152, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 21.9 parts of 2parts of 2-piperidino-4-imino-2-thiazoline hydrochloride in 240 parts of methyl alcohol there was added 14.5 parts of 1,3-diiminoisoindoline. The resultant mixture was heated at reflux for 6 hours, then chilled to 0° C. and filtered. The collected solid was washed with methyl alcohol and dried at 50° C. to obtain 27 parts of 1-imino-3-(2-piperidino-4-imino-2-thiazolin-5-ylidene)isoindoline hydrochloride melting at 320°-321° C. (dec). The assigned chemical structure was completely corroborated by a concordant nuclear magnetic resonance spectrum. The hydrochloride salt is readily converted to the free base, a colorless solid melting at 226°-227° C., by treatment with dilute ammonium hydroxide. This compound, which corresponds to Formula VIII wherein R, R1, R2 and R3 are each hydrogen and N=B is piperidino, was found on testing in vitro by standard serial dilution procedures to be bacteriostatic versus: Staphylococcus aureus 209 at a minimal concentration of 6.3 parts per million; Esherichia coli at 62.5 parts per million; Pseudomonas aeruginosa 211 at 125 parts per million; and fungicidal versus Tricophyton mentogrophytes at 62.5 parts per million; Aspergillus niger at > 125 parts per million; and Candida albicans at 125 parts per million.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationfiltered
  3. washThe collected solid was washed with methyl alcohol
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-bdf5ebbe057d4ce4bcf20f740bcacbd6
Source dataset
uspto-grants-1978_10
Patent number
US04122261

Reaction notes

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