Carbon Dioxide → HCID 131712980, compound

HRID 1701966Notes

Reaction equation

HRID 1701966 reaction equation
I.[NH2:2][C:3]1[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=1.[OH-].[Na+].[O-:12]S([O-])(=O)=O.[Na+].[Na+].C(=O)=O.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[N:30]=[C:31]=[O:32]>C1COCC1>[OH2:12].[ClH:22].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[NH:30][C:31]([NH:2][C:3]1[NH:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]=1)=[O:32].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[NH:30][C:31]([NH:2][C:3]1[NH:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]=1)=[O:32].[ClH:22]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 20504648HCID 20504648, compound

Product 1

HCID 131712980HCID 131712980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 300-ml flask was charged with 12.1 g (0.05 mol) of 2-amino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide 1), 10.0 g of 50% NaOH and 70 ml of THF. After stirring at room temperature for 1 hour, 10.0 g Na2SO4 was added and the mixture was stirred for an additional 1.5 hours. The reaction mixture was cooled to -30° C. (2-PrOH, dry ice) and a solution of 6.3 g (0.033 mol) of 2,6-dichlorophenyl isocyanate in 80 ml of THF was added over a period of 2 hours. At the end of addition, the reaction mixture was allowed to warm to room temperature and stirring continued for 1 hour. The solids, were filtered and the filtrate evaporated in vacuo. The residue was dissolved in dilute HCl, insolubles removed by filtration, and the aqueous solution washed with ether, made basic with cold 30% NaOH, and extracted with CH2Cl2. The combined organic layers were dried (K2CO3), filtered through a pad of diatomaceous earth and evaporated in vacuo. The residue was dissolved in MeOH, neutralized with ethereal HCl and treated with ether to give crystals which were recrystallized from MeOH/ether and then from a minimum amount of H2O to give pure N-(2,6-dichlorophenyl)-N'-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)urea monohydrochloride hemihydrate; m.p. (175) 177°-179° C. dec. UV max. (MeOH) 244 (ε20,100) and 224 nm shld (ε20,800); IR (KBr) 3420, 3200, 1710, 1675, 1535 cm-1.

Workup

  1. stirringthe mixture was stirred for an additional 1.5 hours
  2. additionAt the end of addition
  3. temperatureto warm to room temperature
  4. stirringstirring
  5. waitcontinued for 1 hour
  6. filtrationThe solids, were filtered
  7. customthe filtrate evaporated in vacuo
  8. dissolutionThe residue was dissolved in dilute HCl
  9. custominsolubles removed by filtration
  10. washthe aqueous solution washed with ether
  11. extractionextracted with CH2Cl2
  12. dry with materialThe combined organic layers were dried (K2CO3)
  13. filtrationfiltered through a pad of diatomaceous earth
  14. customevaporated in vacuo
  15. dissolutionThe residue was dissolved in MeOH
  16. additiontreated with ether
  17. customto give crystals which
  18. customwere recrystallized from MeOH/ether

Sources & evidence

ORD record
ord-ad9588b1f3954644b3b54610b855b949
Source dataset
uspto-grants-1983_04
Patent number
US04379786

Reaction notes

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