Dimethylformamide → 2-Acetoxymethyl-5-(benzothiazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74164Notes

Reaction equation

HRID 74164 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:10]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:9]2[CH:17]=[CH:18][C:19]([C:21](O)=O)=[CH:20][C:8]=2[N:7]=1)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[SH:42]>O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[N:10]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:9]2[CH:17]=[CH:18][C:19]([C:21]3[S:42][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[N:35]=3)=[CH:20][C:8]=2[N:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 87132-AminothiophenolHCID 65578Oxalyl chlorideHCID 674979142-Acetoxymethyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid

Product 1

HCID 674980892-Acetoxymethyl-5-(benzothiazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 117.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A 4-neck flask (500 mL) equipped with a reflux condenser was charged with 2-acetoxymethyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid (5.98 g, 18.79 mmol), anhydrous tetrahydrofuran (158 mL), and oxalyl chloride (2.86 g, 22.50 mmol), and anhydrous N,N-dimethylformamide (1 mL) was then added dropwise at room temperature, after which the reaction mixture was stirred at 50° C. for 5 hours. After being allowed to cool to room temperature, the solvent was distilled off under reduced pressure to give a pale yellow residue, which was taken up in anhydrous tetrahydrofuran (100 mL), and then 2-aminobenzenethiol (2.35 g, 18.79 mmol) was added, and this was stirred for 19 hours at 50° C. This was allowed to cool to room temperature, and after the precipitated crystals were filtered off, they were successively washed with distilled water and dried under reduced pressure with heating to yield the title compound (9.00 g, quant.) as a white solid.

Workup

  1. customA 4-neck flask (500 mL) equipped with a reflux condenser
  2. additionwas then added dropwise at room temperature
  3. temperatureto cool to room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a pale yellow residue, which
  6. stirringthis was stirred for 19 hours at 50° C
  7. temperatureto cool to room temperature
  8. filtrationafter the precipitated crystals were filtered off
  9. washthey were successively washed with distilled water
  10. customdried under reduced pressure
  11. temperaturewith heating

Sources & evidence

ORD record
ord-a55a02ffefe847a29485bba91e7d4d06
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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