2-Methylbenzothiazole → HCID 87588516, compound

HRID 1911860Notes

Reaction equation

HRID 1911860 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:11][CH2:12][CH2:13][CH2:14][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>C(OCC)(=O)C>[Br-:11].[CH2:20]([O:19][P:15]([CH2:14][CH2:13][CH2:12][N+:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]=1[CH3:1])([O:16][CH2:17][CH3:18])=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 84462-MethylbenzothiazoleHCID 283500Diethyl (3-bromopropyl)phosphonate

Product 1

HCID 87588516HCID 87588516, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-methybenzothiazole (0.36 g, 2.4 mmol) and diethyl (3-bromopropyl)phosphonate (0.67 g, 2.6 mmol) was heated at 130° C. for 4 hrs. After the mixture was cooled to room temperature, ethyl acetate was added. The precipitate formed was collected by centrifugation, washed with ethyl acetate and dried under vacuum to provide Compound 3 (0.37 g). This product was used without further purification. The structure of Compound 3 is given below:

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. customThe precipitate formed
  3. customwas collected by centrifugation
  4. washwashed with ethyl acetate
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1bf9e4124b024817bd5db419af72f997
Source dataset
uspto-grants-2013_12
Patent number
US08604204B2

Reaction notes

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