3-Chlorotoluene → HCID 178443608, compound

HRID 481966

Reaction equation

HRID 481966 reaction equation
O.CS[C:4]1[NH:9][C:8]2[CH:10]=[CH:11][N:12]=[CH:13][C:7]=2[S:6](=[O:15])(=[O:14])[N:5]=1.[CH2:16]([NH2:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].ClC1C=C(C)C=CC=1>>[CH2:16]([NH:24][C:4]1[NH:9][C:8]2[CH:10]=[CH:11][N:12]=[CH:13][C:7]=2[S:6](=[O:15])(=[O:14])[N:5]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 79313-ChlorotolueneHCID 8143OctylamineHCID 190647513-Methylsulfanyl-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide monohydrate

Product 1

HCID 178443608HCID 178443608, compound

Procedure

A mixture of 3-methylsulfanyl-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide monohydrate (0.5 g), octylamine (0.5 mL) and m-chlorotoluene (3 mL) was refluxed for 2-3 h (until completion of the reaction; t.l.c.). Most of the solvents were removed by distillation and the residue was dispersed in a mixture of water (30 mL) and methanol (30 mL) and supplemented with NaOH 10% w/v in water (2 mL). The mixture was treated with charcoal, filtered, and the filtrate was adjusted to pH 6 with 1N HCl. The resulting precipitate was collected by filtration, washed with water and dried (yield: 0.29 g); m.p. 176°-179° C. (Compound 13).

Workup

  1. temperaturewas refluxed for 2-3 h (
  2. customuntil completion of the reaction
  3. customMost of the solvents were removed by distillation
  4. additionthe residue was dispersed in a mixture of water (30 mL) and methanol (30 mL)
  5. additionThe mixture was treated with charcoal
  6. filtrationfiltered
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water
  9. customdried (yield: 0.29 g)

Sources & evidence

ORD record
ord-5223e56f476842e78541340a7fe3b0ae
Source dataset
uspto-grants-1998_08
Patent number
US05792764

Linked notes

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