Water → HCID 59569037, compound

HRID 1517184Notes

Reaction equation

HRID 1517184 reaction equation
Cl.Br[CH2:3][C:4]([C:6]1[CH:26]=[CH:25][C:9]2[N:10]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)=[N:12][C:8]=2[CH:7]=1)=O.N1C=CC=CC=1.[NH:33]([C:35](=[S:39])[O:36]CC)[NH2:34].O>C(O)C>[CH2:21]([N:10]1[C:9]2[CH:25]=[CH:26][C:6]([C:4]3[CH2:3][S:39][C:35](=[O:36])[NH:33][N:34]=3)=[CH:7][C:8]=2[N:12]=[C:11]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:22]([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12567113O-Ethyl hydrazinecarbothioateHCID 86647278HCID 86647278, compound

Product 1

HCID 59569037HCID 59569037, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 24 g (54.8 mM) of 2-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride in 500 ml of ethanol are added 6.3 ml (78.4 mM) of pyridine and then 8.2 g (78.4 mM) of O-ethyl hydrazinecarbothioate. The reaction medium is then maintained at 80° C. with stirring for 20 hours. Water is then added and the resulting mixture is extracted with ethyl acetate. The organic phase is washed with water and then dried over anhydrous sodium sulfate and evaporated under vacuum. The residue is purified on a column of silica, using a dichloromethane/methanol mixture (98/2). The residue obtained after evaporation is taken up in diethyl ether to give, after filtration, 10 g of 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a light-beige solid.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under vacuum
  5. customThe residue is purified on a column of silica
  6. customThe residue obtained
  7. customafter evaporation
  8. customto give
  9. filtrationafter filtration, 10 g of 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a light-beige solid

Sources & evidence

ORD record
ord-66f8c4d56527458cacf56e77140b54b3
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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