1,2-Dichloroethane → HCID 51201387, compound

HRID 1519229Notes

Reaction equation

HRID 1519229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][CH2:13]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][NH:11][C:18]([CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)=[O:19])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 219302Oxane-4-carboxylic acidHCID 27941942-[(4-chlorophenyl)thio]ethanamine

Product 1

HCID 51201387HCID 51201387, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(4-chlorophenyl)sulfanyl]ethanamine (15.32 g, 82 mmol, prepared from 4-chlorothiophenol and 2-chloroethylamine) in DMF (247 ml) was added sequentially tetrahydro-2H-pyran-4-carboxylic acid (9.66 g, 74.2 mmol), EDC (15.65 g, 82 mmol) and HOAt (2.021 g, 14.85 mmol) and the reaction mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc, washed with 1N HCl, aq NaHCO3, 3M LiCl, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica 1 kg, 50 to 100% EtOAc in hexane), to give N-{2-[(4-chlorophenyl)sulfanyl]ethyl}tetrahydro-2H-pyran-4-carboxamide (18.25 g). MS: M+H=300. H1NMR (400 MHz, CDCl3) δ: 7.31 (d, J=9.9 Hz, 2H), 7.26 (d, J=9.9 Hz, 2H), 5.82 (br s, 1H), 4.40-3.96 (m, 2H), 3.46 (dt, J=7 Hz, 7 Hz, 2H), 3.45-3.36 (m, 2H), 3.05 (t, J=7 Hz, 2H), 2.34-2.26 (m, 1H), 1.82-1.65 (m, 4H).

Workup

  1. washwashed with 1N HCl, aq NaHCO3, 3M LiCl
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (silica 1 kg, 50 to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-1c376a54d33c4788979f63a21d1adb78
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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