Chlorosuccinimide → 2-Chloro-3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal

HRID 1848112Notes

Reaction equation

HRID 1848112 reaction equation
N1CCC[C@H]1C(O)=O.[CH3:9][S:10][C:11]1[S:12][C:13]2[CH:19]=[C:18]([CH2:20][CH2:21][CH:22]=[O:23])[CH:17]=[CH:16][C:14]=2[N:15]=1.[Cl:24]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:24][CH:21]([CH2:20][C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:11]([S:10][CH3:9])[S:12][C:13]=2[CH:19]=1)[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 145742L-ProlineHCID 866810863-(2-(Methylthio)benzo[d]thiazol-6-yl)propanal

Product 1

HCID 866810872-Chloro-3-(2-(methylthio)benzo[d]thiazol-6-yl)propanalYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-proline (0.22 g, 1.9 mmol) was added to a solution of 3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal (2.3 g, 9.7 mmol) in DCM (40 mL) at 0° C. followed by addition of N-chlorosuccinimide (1.4 g, 10 mmol). The reaction mixture was slowly warmed to ambient temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure and purified by silica gel chromatography, eluting with 10:1 to 2:1 petroleum ether/EtOAc to afford 2-chloro-3-(2-(methylthio)benzo[d]thiazol-6-yl)propanal as a yellow oil (2.1 g, 79%). 1H NMR (300 MHz, CDCl3) δ 9.56 (dd, J=1.2, 2.1 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.63 (d, J=0.6 Hz, 1H), 7.28 (d, J=1.5 Hz, 1H), 4.44-4.39 (m, 1H), 3.51-3.44 (m, 1H), 3.20-3.13 (m, 1H), 2.78 (s, 3H). LCMS (ESI) m/z 290 (M+18+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel chromatography
  3. washeluting with 10:1 to 2:1 petroleum ether/EtOAc

Sources & evidence

ORD record
ord-8f0bab065beb491aa91474afc309d9e2
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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