Cyclobutylamine → HCID 178527174, compound

HRID 1975932Notes

Reaction equation

HRID 1975932 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.[CH:14]1([NH2:18])[CH2:17][CH2:16][CH2:15]1>>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:18][CH:14]3[CH2:17][CH2:16][CH2:15]3)[NH:7][C:6]=2[CH:8]=1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178527174HCID 178527174, compoundYield 53%

Conditions

Temperature
0 °C

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (257 mg, 1.0 mmol) in cyclobutylamine (1.0 ml) was stirred for 18 h at 90° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (10 ml) at 0° C. followed by adjustment to pH 2 with 4M hydrochloric acid. The product was isolated by filtration, washed with water, and recrystallised from methanol/ethyl acetate followed by drying in vacuo at room temperature to give 155 mg (53%) of the pure title compound; mp 315-317° C. dec.; 1H-NMR (DMSO-d6): δ1.58-1.75 (m, 2H), 1.89-2.05 (m, 2H), 2.19-2.30 (m, 2H), 4.16 (m, 1H), 7.06 (s, 1H), 7.62 (br s, 1H), 10.83 (br s, 1H); MS: m/e 291/293 (M+); (C9H10N3Cl1O2S2) calc C, 37.05; H, 3.45; N, 14.40; found C, 37.18; H, 3.48; N, 14.19.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customThe product was isolated by filtration
  3. washwashed with water
  4. customrecrystallised from methanol/ethyl acetate
  5. customby drying in vacuo at room temperature

Sources & evidence

ORD record
ord-04ee33a3e48d400bba2bd76f4d8f9060
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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