1,2-Dichloroethane → 2-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-N-propylacetamide

HRID 1480594Notes

Reaction equation

HRID 1480594 reaction equation
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]=[C:9]([S:11][CH2:12][C:13]([OH:15])=O)[S:10][C:6]=2[CH:5]=1)[CH3:2].[CH2:18]([NH2:21])[CH2:19][CH3:20].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]=[C:9]([S:11][CH2:12][C:13]([NH:21][CH2:18][CH2:19][CH3:20])=[O:15])[S:10][C:6]=2[CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7852PropylamineHCID 757711-HydroxybenzotriazoleHCID 9419442-[(6-Ethoxy-1,3-benzothiazol-2-yl)sulfanyl]acetic acid

Product 1

HCID 25688572-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-N-propylacetamideYield 45.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 24 (110.3 mg, 0.41 mmol) and n-propylamine (50.5 mg, 0.50 mmol) in CHCl3 (2.0 ml), HOBt (190 mg, 1.41 mmol) and EDC (120 mg, 0.63 mmol) were added at room temperature. After stirring for 20 hours, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution and brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by HPLC (gradient from 20%, acetonitrile 80% in DDW to 100% acetonitrile, in 15 minutes) to give 33 (57.9 mg, 36% yield) as a brown amorphous solid, range of m.p. temperature was too large for a clear determination. 1H NMR (DMSO-d6): δ 0.97 (t, 3H, J=6.8), δ 1.27 (t, 3H, J=7.1), δ 1.53 (m, 2H, J=6.8, 3.5), δ 3.54 (d, 2H, J=3.7), δ 4.01 (s, 2H), δ 4.19 (q, 2H, J=7.3), δ 6.23 (amide broad peak), δ 6.97 (dd, 1H, J=10.8, J=3.7), 7.33 (d, 2H, J=8.8). 13C NMR (DMSO-d6): δ 12.8, 13.76, 20.6, 39.56, 40.78, 65.1, 101.79, 114.78, 123.6, 135.79, 145.8, 154.67, 168.4, 169.95. MS: MW=310.07 g/mol, MNa+=333.18 g/mol.

Workup

  1. washwashed with saturated NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by HPLC (gradient from 20%, acetonitrile 80% in DDW to 100% acetonitrile, in 15 minutes)

Sources & evidence

ORD record
ord-6ecbf8013fee476bb7a130287d06b5fc
Source dataset
uspto-grants-2016_08
Patent number
US09409904B2

Reaction notes

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