Cyclohexyl isocyanate → HCID 178418526, compound

HRID 2290853Notes

Reaction equation

HRID 2290853 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][SH:25])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1>C(Cl)Cl>[ClH:10].[ClH:10].[CH:1]1([NH:7][C:8](=[SH:25][CH2:24][CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][N:16]([CH2:15][C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:27][CH:26]=3)[CH2:17][CH2:18]2)[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 137311173-[4-(4-Chlorobenzyl)piperazin-1-yl]propanethiol

Product 1

HCID 178418526HCID 178418526, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of cyclohexyl isocyanate, 2.1 g of 3-[4-(4-chlorobenzyl)piperazin-1-yl]propanethiol and 10 ml of methylene chloride was stirred at room temperature overnight and then concentrated in vacuo. The residue crystallized upon standing. The product was recrystallized from aqueous ethanol, dissolved in ether, and the ethanol solution was dried (magnesium sulfate). The salt was then precipitated with ethereal hydrochloric acid and recrystallized twice from aqueous ethanol to give 1.2 g (30% of theory) of N-cyclohexyl-S-{3-[4-(4-chlorobenzyl)piperazin- 1-yl]propyl}thiocarbamate dihydrochloride as a white crystalline solid, M.p. >165° C. (dec.).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue crystallized
  3. customThe product was recrystallized from aqueous ethanol
  4. dissolutiondissolved in ether
  5. dry with materialthe ethanol solution was dried (magnesium sulfate)
  6. customThe salt was then precipitated with ethereal hydrochloric acid
  7. customrecrystallized twice from aqueous ethanol

Sources & evidence

ORD record
ord-73fb518343bf46899514354c659c4b0d
Source dataset
uspto-grants-1986_10
Patent number
US04618677

Reaction notes

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