Carbon Disulfide → HCID 14518047, compound

HRID 1904845Notes

Reaction equation

HRID 1904845 reaction equation
[C:1](=[S:3])=S.[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=[C:13]2[CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)=[CH:7][CH:6]=1.[C:35]1([CH2:41][N:42]2[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]=[C:43]2[CH2:51][CH:52]2[CH2:57][CH2:56][N:55]([CH2:58][CH2:59][NH2:60])[CH2:54][CH2:53]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=[C:13]2[CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26][CH2:27]2)=[CH:7][CH:6]=1.[N:60]([CH2:59][CH2:58][N:55]1[CH2:56][CH2:57][CH:52]([CH2:51][C:43]2[N:42]([CH2:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]=2)[CH2:53][CH2:54]1)=[C:1]=[S:3]

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14518046HCID 14518046, compoundHCID 20037933HCID 20037933, compound

Product 2

HCID 14518047HCID 14518047, compoundYield 89%HCID 20037933HCID 20037933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (-10° C.) mixture of 20.8 parts of carbon disulfide, 9 parts of N,N'-methanetetraylbis[cyclohexanamine] and 135 parts of tetrahydrofuran was added dropwise a solution of 15 parts of 4-[[1-(phenylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidineethanamine in tetrahydrofuran at a temperature below -10° C. The reaction mixture was allowed to reach room temperature and the solvent was evaporated. The residue was crystallized from acetonitrile. The precipitate was filtered off and the filtrate was evaporated, yielding 15 parts (89%) of 2-[[1-(2-isothiocyanatoethyl)4-piperidinyl]methyl]-1-(phenylmethyl)-1H-benzimidazole (395).

Workup

  1. temperaturecooled
  2. customto reach room temperature
  3. customthe solvent was evaporated
  4. customThe residue was crystallized from acetonitrile
  5. filtrationThe precipitate was filtered off
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-baa2c4b8d192443d93ab3c1ad436332b
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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