Methane → HCID 178527170, compound

HRID 2268741Notes

Reaction equation

HRID 2268741 reaction equation
Cl[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([Cl:11])[S:10][C:5]=2[S:4](=[O:13])(=[O:12])[N:3]=1.Cl.[C:15]12([NH2:25])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.C(N(CC)CC)C.C>C(O)C.[OH-].[Na+]>[C:15]12([NH:25][C:2]3[NH:7][C:6]4[CH:8]=[C:9]([Cl:11])[S:10][C:5]=4[S:4](=[O:13])(=[O:12])[N:3]=3)[CH2:22][CH:21]3[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]3)[CH2:16]1)[CH2:24]2

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 64150Amantadine HydrochlorideHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178527170HCID 178527170, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (1.0 g, 3.9 mmol), 1-adamantanamine hydrochloride (1.46 g, 7.8 mmol) and triethylamine (1.1 ml, 7.8 mmol) in ethanol (6 ml) was stirred for 41 h at 120° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (50 ml) followed by adjustment to pH <2 with 4M hydrochloric acid. The resulting dark mass was isolated by decantation and then partly dissolved in hot 1N sodium hydroxide (50 ml) followed by treatment with decolourising charcoal. After filtration, the solution was acidified to pH <2 and the precipitate was filtered off and recrystallised from ethanol to give 160 mg (11%) of the title compound as a beige solid; mp 339-340° C.; 1H-NMR (DMSO-d6): δ1.64 (br s, 6H), 2.02 (br s, 6H), 2.06 (br s, 3H), 6.67 (br s, 1H), 7.10 (s, 1H), 10.55 (br s, 1H); MS: m/e 371/373 (M+); (C15H18ClN3O2S2) calc C, 48.44; H, 4.88; N, 11.30; found C, 48.27; H, 4.85; N, 11.15.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. stirringthe residue was stirred with water (50 ml)
  3. customThe resulting dark mass was isolated by decantation
  4. filtrationAfter filtration
  5. filtrationthe precipitate was filtered off
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-ad51dc75b0c2457ba791d621483d538d
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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