HCID 176526843, compound → HCID 178508737, compound

HRID 1833501Notes

Reaction equation

HRID 1833501 reaction equation
Cl.[NH:2]=[C:3]1[NH:7][C:6](=[NH:8])[CH2:5][S:4]1.[NH:9]=[C:10]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12](=N)[NH:11]1>CO>[NH:9]=[C:10]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12](=[C:5]2[S:4][C:3](=[NH:2])[NH:7][C:6]2=[NH:8])[NH:11]1

Participants

4

Reactant 2

HCID 176526843HCID 176526843, compoundHCID 178479111HCID 178479111, compound

Product 1

HCID 178508737HCID 178508737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6 parts of 2,4-diiminothiazolidine hydrochloride, 6 parts of 4,5,6,7-tetrahydro-1,3-diiminoisoindoline and 100 parts of anhydrous methyl alcohol was stirred and heated at reflux under an atmosphere of nitrogen for approximately 16 hours. The reaction was then cooled and filtered. The solid product collected by filtration was converted to the free base by treatment with a slight excess of a methyl alcohol solution of triethylamine and the product thus obtained was recrystallized from acetic acid. The resultant acetate salt was treated with dilute ammonium hydroxide and the product isolated to obtain in the free-base form 1-imino-4,5,6,7-tetrahydro-3-(2,4-diimino-5-thiazolidinylidene)isoindoline as a greenish-brown powder melting at 215°-223° C (dec).

Workup

  1. temperatureheated
  2. temperatureat reflux under an atmosphere of nitrogen for approximately 16 hours
  3. temperatureThe reaction was then cooled
  4. filtrationfiltered
  5. filtrationThe solid product collected by filtration
  6. customthe product thus obtained
  7. customwas recrystallized from acetic acid
  8. additionThe resultant acetate salt was treated with dilute ammonium hydroxide
  9. customthe product isolated

Sources & evidence

ORD record
ord-77445322b1dc4077a85978a2e07b7efa
Source dataset
uspto-grants-1978_01
Patent number
US04066653

Reaction notes

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