Hydrochloric Acid → HCID 178454510, compound

HRID 2268739Notes

Reaction equation

HRID 2268739 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.[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17].Cl>O>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[NH:7][C:6]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 118072-Amino-2-methyl-1-propanolHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178454510HCID 178454510, compoundYield 14.1%

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 (0.3 g, 1.17 mmol) in 2-amino-2-methyl-1-propanol (2 ml, 21 mmol) was stirred for 40 h at 120° C. in a sealed flask. Water (5 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 recrystallised from methanol/water to give 51 mg (14%) of the pure title compound; mp 224-226° C.; 1H-NMR (DMSO-d6): δ1.30 (s, 6H), 3.43 (s, 2H), 5,17 (br s, 1H), 6.63 (br s, 1H), 7.10 (s, 1H), 10.90 (s, 1H); MS: m/e 309/311 (M+).

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with water
  3. customrecrystallised from methanol/water

Sources & evidence

ORD record
ord-a2173869c29e4c0583418f59b4a02a5f
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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