Carbon Disulfide → HCID 20385654, compound

HRID 2420350Notes

Reaction equation

HRID 2420350 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:11][CH2:10]1.[C:28](=S)=[S:29]>C(O)C>[S:29]=[C:28]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:27])[CH2:13][CH2:14]2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 20385649HCID 20385649, compound

Product 1

HCID 20385654HCID 20385654, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18.3 parts of 1-[3-{4-[(2-aminophenyl)amino]-1-piperidinyl}propyl]-1,3-dihydro-2H-benzimidazol-2-one, 65 parts of carbon disulfide and 60 parts of ethanol is stirred and refluxed for 24 hours. The reaction mixture is evaporated. The residue is crystallized from ethanol. The product is filtered off and dried, yielding 4.5 parts (19.7%) of 1-{3-[4-(2,3-dihydro-2-thioxo-1H-benzimidazol-1-yl)-1-piperidinyl]propyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 248.5° 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. customdried

Sources & evidence

ORD record
ord-c6c6f13e696f4d00af04e1ee67c90458
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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