Benzoic acid, 2-mercapto-, methyl ester → 2,3,4,5-Tetrahydro-1,4-benzothiazepin-5-one

HRID 539946Notes

Reaction equation

HRID 539946 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.Cl.Cl[CH2:14][CH2:15][NH2:16].[H-].[Na+]>O1CCCC1.CN(C)C=O>[S:1]1[C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4](=[O:6])[NH:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 24758Sodium hydrideHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 52270982,3,4,5-Tetrahydro-1,4-benzothiazepin-5-oneYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of methyl 2-sulfanylbenzoate (200 g, 1.19 mol) in tetrahydrofuran and N,N-dimethylformamide (2 L, V/V=1/1) was added 2-chloroethanamine hydrochloride (138 g, 1.19 mol) at 0° C. followed by sodium hydride (143 g, 3.57 mol, 60% in mineral oil) in portions. After being stirred at room temperature overnight, the reaction mixture was poured into ice-water and extracted with ethyl acetate (900 mL×4). The organic layers were combined, washed with brine (900 mL×3), dried over sodium sulfate and concentrated in vacuo. The residue was stirred in a mixture solution of ethyl acetate and petroleum ether (300 mL, V/V=1/1) for 1 hour. The solid was collected by filtration and dried in vacuo to afford 100 g of 3,4-dihydro-1,4-benzothiazepin-5(2H)-one (yield was 47%).

Workup

  1. extractionextracted with ethyl acetate (900 mL×4)
  2. washwashed with brine (900 mL×3)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. stirringThe residue was stirred in a mixture solution of ethyl acetate and petroleum ether (300 mL, V/V=1/1) for 1 hour
  6. filtrationThe solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-686baff3886f4b1495c987227ac34edb
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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