1,1'-Thiocarbonyldiimidazole → HCID 14625410, compound

HRID 2107818Notes

Reaction equation

HRID 2107818 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12][NH:11]1)([O-])=O.[C:24](N1C=CN=C1)(N1C=CN=C1)=[S:25]>COCCOC>[C:18]1([CH2:17][N:14]2[CH2:15][CH2:16][N:10]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH:1][C:24](=[S:25])[N:11]3[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 14625404HCID 14625404, compound

Product 1

HCID 14625410HCID 14625410, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Hexahydro-1-(2-nitrophenyl)-5-(phenylmethyl)-1H-1,2,5-triazepine (10.0 g) was hydrogenated in 1,2-dimethoxyethane (250 ml) as in example 11 and the volume reduced to approximately 150 ml. 1,1'-Thiocarbonyldiimidazole (20 g) was added and the solution refluxed with protection from moisture overnight. The solution was evaporated to dryness and the residue, dissolved in chloroform, was applied to a column (72×6.3 cm) of dry column grade neutral alumina prepacked in chloroform. Elution with chloroform provided a major component. Evaporation of appropriate fractions gave a product which was difficult to crystallize. This material was subjected to further fractionation on a column (67.5×4.2 cm) of the same absorbent with chloroform as eluting solvent. Fractions were monitored by t.l.c. on Alox-25 uv254 plates with ethyl acetate as developer. Evaporation of homogenous fractions provided material which was crystallized from chloroform-heptane; wt. 5.35 (51%), mp=124°-126°. Recrystallization (with decolorization) from the same solvents gave pure titled product, mp=125°-127°.

Workup

  1. temperaturethe solution refluxed with protection from moisture overnight
  2. customThe solution was evaporated to dryness
  3. dissolutionthe residue, dissolved in chloroform
  4. washElution with chloroform
  5. customprovided a major component
  6. customEvaporation of appropriate fractions
  7. customgave a product which
  8. customto crystallize
  9. washas eluting solvent
  10. customEvaporation of homogenous fractions
  11. customprovided material which
  12. customwas crystallized from chloroform-heptane
  13. customRecrystallization (with decolorization) from the same solvents

Sources & evidence

ORD record
ord-06bab6e7d6d74a2a999b406fdd4d34aa
Source dataset
uspto-grants-1990_06
Patent number
US04935515

Reaction notes

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