1-Methylcyclopropanamine → HCID 178432420, compound

HRID 2268738Notes

Reaction equation

HRID 2268738 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]1([NH2:18])[CH2:17][CH2:16]1>>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:18][C:15]3([CH3:14])[CH2:17][CH2:16]3)[NH:7][C:6]=2[CH:8]=1

Participants

3

Reactant 2

HCID 116511491-MethylcyclopropanamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178432420HCID 178432420, compoundYield 26%

Procedure

A solution of 3,6-dichloro4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (386 mg, 1.5 mmol) in 1-methylcyclopropylamine (1.0 g, 14 mmol) was stirred for 24 h at 85° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with ethyl acetate (1-2 ml) and filtered. The white precipitate was stirred in 4M hydrochloric acid (5 ml) for 2 h and then filtered off and chromatographed on silica gel with ethyl acetate to give 112 mg (26%) of the pure title compound; mp 251-252° C. dec; 1H-NMR (DMSO-d6): δ0.65-0.79 (m, 4H), 1.36 (s, 3H), 7.11 (s, 1H), 7.82 (br s, 1H), 10.78 (br s, 1H); MS: m/e 291/293 (M+); (C9H10N3Cl1O2S2) calc. C, 37.05; H, 3.45; N, 14.40; found C, 36.96; H, 3.53; N, 14.15.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. filtrationfiltered
  3. stirringThe white precipitate was stirred in 4M hydrochloric acid (5 ml) for 2 h
  4. filtrationfiltered off
  5. customchromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-fd6e37bbb2e541c8a63ec5aa187fc69c
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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