Ethylenediamine → HCID 178511337, compound

HRID 1066155Notes

Reaction equation

HRID 1066155 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](SC)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[CH2:16]([NH2:19])[CH2:17][NH2:18]>>[OH2:10].[NH2:18][CH2:17][CH2:16][NH:19][C:7]1[NH:6][C:5]2[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][C:4]=2[S:9](=[O:11])(=[O:10])[N:8]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 127001067-Chloro-3-(methylthio)-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178511337HCID 178511337, compound

Conditions

Temperature
0 °C

Procedure

A solution of 7-chloro-3-methylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide (1 g) in ethylenediamine (2.5 mL) was refluxed for 45 min. Most of the excess of amine was removed by distillation under reduced pressure and the resulting oily residue was dissolved in methanol (10 mL). Addition of diethylether (40 mL) gave rise to the precipitation of an oil which turned to a white solid after a stirring of 30 min. at 0° C. The precipitate was collected by filtration, washed with diethylether and dried. The solid was dissolved in boiling water (40 mL) and traces of insoluble material were removed by filtration. The filtrate was concentrated to the half volume by distillation under reduced pressure and placed at +4° C. for 2 h. The crystalline precipitate of the title compound was cpllected by filtration, washed with a small volume of water and dried to give the title compound (yield: 0.62 g); m.p. 200-204° C.; IR (KBr): 3498, 3372, 2932, 1637, 1560, 1481, 1264, 1163 cm−1; 1H-NMR (DMSO-d6, HMDS; δ ppm): 2.70 (t, 2H, NH—CH2—CH2—NH2), 3.20 (t, 2H, NH—CH2—CH2—NH2), 5.25 (b, 6H, 2×NH+H2O+NH2), 6.95 (d, 1H, 5-H), 7,30 (d, 1H, 6-H), 7.45 (s, 1H, 8-H).

Workup

  1. customMost of the excess of amine was removed by distillation under reduced pressure
  2. dissolutionthe resulting oily residue was dissolved in methanol (10 mL)
  3. additionAddition of diethylether (40 mL)
  4. customgave rise
  5. customto the precipitation of an oil which
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with diethylether
  8. customdried
  9. dissolutionThe solid was dissolved
  10. customwere removed by filtration
  11. concentrationThe filtrate was concentrated to the half volume by distillation under reduced pressure
  12. waitplaced at +4° C. for 2 h
  13. filtrationThe crystalline precipitate of the title compound was cpllected by filtration
  14. washwashed with a small volume of water
  15. customdried

Sources & evidence

ORD record
ord-2e72ff17822549458d77008063f569ae
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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