Carbon Disulfide → HCID 20385636, compound

HRID 46909Notes

Reaction equation

HRID 46909 reaction equation
[C:1](=[S:3])=S.[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:25]3[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=3[NH:23][C:22]2=[O:31])[CH2:17][CH2:16]1>C(O)C>[Cl:30][C:28]1[CH:27]=[CH:26][C:25]2[N:21]([CH:18]3[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][N:11]4[C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[NH:4][C:1]4=[S:3])[CH2:16][CH2:17]3)[C:22](=[O:31])[NH:23][C:24]=2[CH:29]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 203856041-[1-{3-[N-(2-aminophenyl)amino]propyl}-4-piperidinyl]-5-chloro-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 20385636HCID 20385636, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 38 parts of carbon disulfide, 6 parts of 1-[1-{3-[N-(2-aminophenyl)amino]propyl}-4-piperidinyl]-5-chloro-1,3-dihydro-2H-benzimidazol-2-one and 32 parts of ethanol is stirred and refluxed for 24 hours. The reaction mixture is evaporated and the residue is crystallized from ethanol. The product is filtered off and recrystallized from a mixture of N,N-dimethylformamide and water, yielding 3 parts (45.5%) of 5-chloro-1-{1-[3-(2,3-dihydro-2-thioxo-1H-benzimidazol-1-yl)-propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 266.6° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue is crystallized from ethanol
  4. filtrationThe product is filtered off
  5. customrecrystallized from a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-bd224c318ab045c8ae2d4754fb60a869
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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