2-Butanamine, (S)- → HCID 178456036, compound

HRID 1975924Notes

Reaction equation

HRID 1975924 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.[C@@H:14]([NH2:18])([CH2:16][CH3:17])[CH3:15]>C(O)C>[C@@H:14]([NH:18][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)([CH2:16][CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 67137532-Butanamine, (S)-HCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178456036HCID 178456036, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (257 mg, 1.0 mmol) and (S)-(+)-sec-butylamine (0.31 ml, 3.0 mmol) was stirred in 10 ml of abs ethanol for 4 days at 80° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (10 ml) followed by adjustment to pH 2 with 4M hydrochloric acid. The initially formed gummy product was crystallized by stirring at 0° C. The precipitate was isolated by filtration, washed with water, and recrystallised from ethyl acetate/methanol followed by drying in vacuo at 30° C. over night to give 181 mg (62%) of the pure title compound; mp 228-230° C. (ethyl acetate); 1H-NMR (DMSO-d6): δ0.88 (t, 3H, CH3), 1.14 (d, 3H, CH3), 1,49 (m, 2H, CH2), 3.68 (m, 1H, CH), 7.08 (s, 1H, H-5), 7.13 (br, 1H, NH), 10.73 (br s, 1H, NH); MS: m/e 293/295 (M+); (C9H12N3Cl1O2S2) calc. C, 36.79; H, 4.12; N, 14.30; found C, 36.9; H, 4.1; N, 14.2.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customThe initially formed gummy product was crystallized
  3. stirringby stirring at 0° C
  4. customThe precipitate was isolated by filtration
  5. washwashed with water
  6. customrecrystallised from ethyl acetate/methanol
  7. customby drying in vacuo at 30° C. over night

Sources & evidence

ORD record
ord-bc175d7826954227b8bfca306d4142c6
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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