Hydrochloric Acid → HCID 178462357, compound

HRID 1975934Notes

Reaction equation

HRID 1975934 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.[OH2:14].Cl>NC[C@H](O)C>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:7][CH2:6][C@H:8]([OH:14])[CH3:9])[NH:7][C:6]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178462357HCID 178462357, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 439938(2R)-1-aminopropan-2-olSolvent

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (200 mg, 0.78 mmol) in (R)-(−)-1-amino-2-propanol (1.0 ml) was stirred for 18 h at 100° C. in a sealed flask. The cooled solution was stirred with water (3 ml) at 0° C. followed by adjustment to pH 2 with 4M hydrochloric acid. The product was isolated by filtration, washed with water, and dried in vacuo at room temperature to give 170 mg (74%) of the pure title compound; mp 210-211° C.; 1H-NMR (DMSO-d6): δ1.08 (d, 3H), 3.0-3.1 (m, 1H), 3.15-3.25 (m, 1H), 3.72-3.82 (m, 1H), 4.91 (br s, 1H), 7.09 (s, 1H), 7.14 (br s, 1H), 10.95 (br s, 1H); MS: m/e 297/295(M+); (C8H10N3Cl1O3S2 .0.5 H2O) calc C, 31.53; H, 3.64; N, 13.79; found C, 31.57; H, 3.58; N, 13.58.

Workup

  1. customThe product was isolated by filtration
  2. washwashed with water
  3. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-2db3757365e142af9c9971903da5c4df
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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