Hydrochloric Acid → HCID 178443609, compound

HRID 2268740Notes

Reaction equation

HRID 2268740 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.[CH3:14][C:15]([NH2:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].Cl>O>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:22][C:15]([CH3:21])([CH3:14])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH:7][C:6]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61017tert-OctylamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178443609HCID 178443609, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (0.5 g, 1.95 mm0l) in 1,1,3,3-tetramethylbutylamine (5 ml, 31 mmol) was stirred for 44 h at 120° C. in a sealed flask. Water (25 ml) was added to the cooled solution and pH was adjusted to <2 by the addition of 4M hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water, and then redissolved in 1N sodium hydroxide (15 ml) at 50-60° C. followed by treatment with decolorising charcoal. After filtration, the clear solution was acidified to pH 2 by the addition of 4M hydrochloric acid and the precipitate was filtered off and recrystallised from methanol to give 207 mg (31%) of the pure title compound; mp 369-371° C. dec; 1H-NMR (DMSO-d6): δ0.98 (s, 9H), 1.42 (s, 6H), 1,86 (s, 2H), 6.75 (br s, 1H), 7,12 (s, 1H), 10.55 (s, 1H); MS: m/e 349/351 (M+); (C13H20N3Cl1O2S2) calc. C, 44.63; H, 5.76; N, 12.01; found C, 44.74; H, 5.78; N, 11.84.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with water
  3. dissolutionredissolved in 1N sodium hydroxide (15 ml) at 50-60° C.
  4. filtrationAfter filtration
  5. additionthe clear solution was acidified to pH 2 by the addition of 4M hydrochloric acid
  6. filtrationthe precipitate was filtered off
  7. customrecrystallised from methanol

Sources & evidence

ORD record
ord-f157524ac0b649acaa32ca50521cb5e0
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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