2-Bromoethylamine hydrobromide → HCID 11469493, compound

HRID 1109580Notes

Reaction equation

HRID 1109580 reaction equation
[SH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.Br.[NH2:12][CH2:13][CH2:14]Br.C[O-].[Na+]>C1(C)C=CC=CC=1.CO>[S:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:9])[NH:12][CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 27742172-Bromoethylamine hydrobromideHCID 10942334Sodium MethoxideHCID 19020440HCID 19020440, compound

Product 1

HCID 11469493HCID 11469493, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

aca) Method A: 17.4 g of methyl 3-mercapto-thiophene-2-carboxylate were dissolved in 350 ml of toluene under an inert gas atmosphere, whereupon the solution was treated with 20.5 g of 2-aminoethyl bromide hydrobromide and then with 100 ml of 3N sodium methylate solution in methanol. The mixture was stirred at room temperature for 30 minutes and thereafter heated under reflux until the reaction finished. The mixture was evaporated in vacuo, the residue was taken up in 300 ml of water, acidified with 2N hydrochloric acid and the crystals were removed by filtration. By recrystallization from chloroform there was obtained 3,4-dihydro-thieno[2,3-f][1,4]thiazepin-5-(2H)-one as white crystals of m.p. 186°-188°.

Workup

  1. temperatureheated
  2. temperatureunder reflux until the reaction
  3. customThe mixture was evaporated in vacuo
  4. customthe crystals were removed by filtration
  5. customBy recrystallization from chloroform

Sources & evidence

ORD record
ord-02800629570d4235a3666cf27be683dd
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

Loading…