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

HRID 507243Notes

Reaction equation

HRID 507243 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-f11d7f8bef724a91b0eb7588473d5388
Source dataset
uspto-grants-2010_08
Patent number
US07786137B2

Reaction notes

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