Carbon Disulfide → HCID 178527773, compound

HRID 354994Notes

Reaction equation

HRID 354994 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.[C:32](=S)=[S:33].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:20]1([CH:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:16]2[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][CH2:10][N:9]3[C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[N:2]=[C:32]3[SH:33])[CH2:18][CH2:17]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 10340Sodium CarbonateHCID 20506359N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine hydrochloride

Product 1

HCID 178527773HCID 178527773, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.37 parts of N-(2-aminophenyl)-4-(diphenylmethyl)-1-piperazinepropanamine hydrochloride, 38 parts of carbon disulfide, 2 parts of sodium carbonate and 40 parts of ethanol is stirred and refluxed for 20 hours. The reaction mixture is evaporated and water is added to the residue. The precipitated product is filtered off, washed with water and dissolved in trichloromethane. The solution is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 1-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-1H-benzimidazole-2-thiol; mp 181.8° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. filtrationThe precipitated product is filtered off
  5. washwashed with water
  6. dissolutiondissolved in trichloromethane
  7. customThe solution is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-b9b1dfd4852d49bbba322e59047578b8
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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