2-Methylallylamine → HCID 178448911, compound

HRID 1975939Notes

Reaction equation

HRID 1975939 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.[CH2:14]([NH2:18])[C:15](=[CH2:17])[CH3:16]>>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:18][CH2:14][C:15]([CH3:17])=[CH2:16])[NH:7][C:6]=2[CH:8]=1

Participants

3

Reactant 2

HCID 761412-MethylallylamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178448911HCID 178448911, compoundYield 64%

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (128 mg, 0.5 mmol) in methallylamine (0.5 ml) was stirred for 48 h at 90° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (3 ml) followed by adjustment to pH 2 with 4M hydrochloric acid. The product was isolated by filtration and washed with water, to give 92 mg (64%) of the pure title compound; mp 224-226° C. (dec.); 1H-NMR (DMSO-d6): δ1.72 (s, 3H), 3.75 (d, 2H), 4.83 (s, 2H), 7.05 (s, 1H), 7.45 (br s, 1H), 11.0 (br s, 1H).

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customThe product was isolated by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-8b04ab35c5fd4268a133f3634da2cb55
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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