2-Butanamine, 2-methyl- → HCID 178446298, compound

HRID 2268737Notes

Reaction equation

HRID 2268737 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]([NH2:19])([CH3:18])[CH2:16][CH3:17]>>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:19][C:15]([CH3:18])([CH3:14])[CH2:16][CH3:17])[NH:7][C:6]=2[CH:8]=1

Participants

3

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178446298HCID 178446298, compoundYield 56.5%

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (5.0 g, 19.45 mmol) in 1,1-dimethylpropylamine (10 ml, 85.7 mmol) was stirred for 30 h at 125° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (25 ml) followed by adjustment to pH 2 with 4M hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water, and then redissolved by slightly heating in 1N sodium hydroxide (130 ml) followed by treatment with decolorising charcoal. After filtration, the clear solution was acidified to pH 2 and the precipitate was filtered off and recrystallised from methanol to give 3.38 g (56%) of the pure title compound; mp 359-360° C.; 1H-NMR (DMSO-d6): δ0.82 (t, 3H), 1.31 (s, 6H), 1,73 (q, 2H), 6.67 (br s, 1H), 7,12 (s, 1H), 10.57 (br s, 1H); MS: m/e 307/309 (M+); (C10H14N3Cl1O2S2) calc. C, 39.02; H, 4.58; N, 13.65; Cl, 11.52; S, 20.83; found C, 39.10; H, 4.58; N, 13.48; Cl, 11.69; S, 20.97.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. dissolutionredissolved
  5. temperatureby slightly heating in 1N sodium hydroxide (130 ml)
  6. filtrationAfter filtration
  7. filtrationthe precipitate was filtered off
  8. customrecrystallised from methanol

Sources & evidence

ORD record
ord-d40ecbfee6eb4808a6f2829034dd2755
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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