1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-n-(thiazol-2-yl)indoline-5-sulfonamide

HRID 1809342Notes

Reaction equation

HRID 1809342 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH2:14][CH2:13]2)(=[O:9])=[O:8].CCN(CC)CC.Br[CH2:27][CH2:28][Cl:29]>CN(C=O)C>[Cl:29][CH2:28][CH2:27][N:15]1[C:16]2[C:12](=[CH:11][C:10]([S:7]([NH:6][C:2]3[S:1][CH:5]=[CH:4][N:3]=3)(=[O:9])=[O:8])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 8471TriethylamineHCID 43119856HCID 43119856, compound

Product 1

HCID 594328791-(2-Chloroethyl)-n-(thiazol-2-yl)indoline-5-sulfonamideYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2,3-dihydro-1H-indole-5-sulfonic acid thiazol-2-ylamide (10.0 g, 35.6 mmol), Et3N (5.0 mL, 3.6 g, 35.6 mmol), and DMF (10.0 mL), under N2, was added 1-bromo-2-chloroethane (2.9 mL, 5.1 grams, 35.6 mmol). The solution was stirred at room temperature for 3 days. The mixture was partitioned between water and ethyl acetate. The organic portion was evaporated to dryness under reduced pressure. The residue was purified via silica gel chromatography using 3% MeOH in CH2Cl2 to obtain the desired amine (3.1 g, 9.0 mmol, 25% yield) as a clear oil. 1H-NMR (DMSO-d6) δ 7.39-7.37 (m, 2H), 6.83 (d, J=4.7 Hz, 1H), 6.43 (d, J=7.3 Hz, 2H), 6.28 (s, 1H), 4.23 (t, J=5.8 Hz, 2H), 3.88 (t, J=5.8 Hz, 2H), 3.47 (t, J=8.7 Hz, 2H), 3.33 (s, 1H), 2.94 (t, J=3.7 Hz, 2H). LC/MS (10-99%) M/Z: M+1 obs=344.0; tR=2.88 min.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customThe organic portion was evaporated to dryness under reduced pressure
  3. customThe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-c16fc0d803584888bf5d6ea44e7686c8
Source dataset
uspto-grants-2013_01
Patent number
US08362032B2

Reaction notes

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