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Hydrochloric Acid → 5-(2-Methylsulphonylaminomethylpropan-2-yl)-2-(2-methoxy-4-methylmercaptophenyl)-benzimidazole

HRID 1639143
Notes
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Reaction equation

HRID 1639143 reaction equation
[C:1](NCC(C1C=CC(N)=C(N)C=1)(C)C)(=O)C.[S:17](=[O:20])(O)[O-:18].COC1C=C(SC)C=CC=1C=O.COC1C=C(SC)C=CC=1C1NC2C=CC=CC=2N=1.Cl.[NH2:53][CH2:54][C:55]([C:58]1[CH:76]=[CH:75][C:61]2[N:62]=[C:63]([C:65]3[CH:70]=[CH:69][C:68]([S:71][CH3:72])=[CH:67][C:66]=3[O:73][CH3:74])[NH:64][C:60]=2[CH:59]=1)([CH3:57])[CH3:56]>C(O)C.CO>[CH3:1][S:17]([NH:53][CH2:54][C:55]([C:58]1[CH:76]=[CH:75][C:61]2[N:62]=[C:63]([C:65]3[CH:70]=[CH:69][C:68]([S:71][CH3:72])=[CH:67][C:66]=3[O:73][CH3:74])[NH:64][C:60]=2[CH:59]=1)([CH3:57])[CH3:56])(=[O:20])=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 104748BisulfiteHCID 124333932-Methoxy-4-(methylsulfanyl)benzaldehydeHCID 141530264-(2-Acetamidomethylprop-2-yl)-1,2-diaminobenzeneHCID 198404585-(2-Aminomethylpropan-2-yl)-2-(2-methoxy-4-methylmercaptophenyl)-benzimidazoleHCID 867435222-(2-Methoxy-4-methylmercaptophenyl)-benzimidazole

Product 1

HCID 539683705-(2-Methylsulphonylaminomethylpropan-2-yl)-2-(2-methoxy-4-methylmercaptophenyl)-benzimidazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Air is passed into a solution of 13 g. of 4-(2-acetamidomethylprop-2-yl)-1,2-diaminobenzene (obtained in Example 1f) and 18 g. of the bisulphite adduct of 2-methoxy-4-methylmercaptobenzaldehyde in 500 ml. methanol for 8 hours at ambient temperature. The reaction mixture is then evaporated and the residue purified by column chromatography (1.5 liters silica gel; trichloromethane:methanol:glacial acetic acid 10:1:0.2 v/v/v). There are obtained 16 g. 5-(2-acetamidomethylpropan-2-yl)-2-yl)-2-(2-methoxy-4-methylmercaptophenyl)-benzimidazole in the form of a brownish viscous mass which is boiled under reflux in 400 ml. ethanol and 100 ml. concentrated hydrochloric acid for 3 days. The reaction mixture is then evaporated and the residue is rendered alkaline with 2N aqueous sodium hydroxide solution and extracted with dichloromethane. The product is purified by column chromatography (silica gel; dichloromethane/methanolic ammonia 10:1 v/v) to give 5.4 g. 5-(2-aminomethylpropan-2-yl)-2-(2-methoxy-4-methylmercaptophenyl)-benzimidazole in the form of a brownish viscous mass, as well as 1 g. of unreacted starting material. 2.7 g. of the product are mesylated analogously to Example 33 to give 3.1 g. of the title compound in the form of a dihydrate; m.p 237°-239° C.

Workup

  1. customThe reaction mixture is then evaporated
  2. customthe residue purified by column chromatography (1.5 liters silica gel; trichloromethane:methanol:glacial acetic acid 10:1:0.2 v/v/v)
  3. customThere are obtained 16 g
  4. temperatureunder reflux in 400 ml
  5. customThe reaction mixture is then evaporated
  6. extractionextracted with dichloromethane
  7. customThe product is purified by column chromatography (silica gel; dichloromethane/methanolic ammonia 10:1 v/v)
  8. customto give 5.4 g
  9. customto give 3.1 g

Sources & evidence

ORD record
ord-e73e8b7cf7db431e9a454c6611b41c74
Source dataset
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04882342

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes