Phenyl isocyanate → HCID 178418533, compound

HRID 2290848Notes

Reaction equation

HRID 2290848 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:10].Cl.[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][SH:28])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[OH2:9].[ClH:10].[ClH:10].[C:1]1([NH:7][C:8](=[SH:28][CH2:27][CH2:26][CH2:25][N:22]2[CH2:21][CH2:20][N:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:24][CH2:23]2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 137311143-(4-Benzylpiperazin-1-yl)propanethiol dihydrochloride

Product 1

HCID 178418533HCID 178418533, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.6 g of phenyl isocyanate were added to a solution of 4.0 g of 3-(4-benzylpiperazin-1-yl)propanethiol dihydrochloride and 2.6 g of triethylamine in 50 ml of methylene chloride. The mixture was refluxed for four hours, washed with water and dried (sodium sulfate). Precipitation of the salt with ethereal hydrochloric acid gave 1.2 g (20% of theory) of N-phenyl-S-[3-(4-benzylpiperazin-1-yl)-propyl]thiocarbamate dihydrochloride monohydrate as a white crystalline solid, M.p. 216°-219° C.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. washwashed with water
  3. dry with materialdried (sodium sulfate)
  4. customPrecipitation of the salt with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-359828d1f9d14ebdae58f5c01167e6d2
Source dataset
uspto-grants-1986_10
Patent number
US04618677

Reaction notes

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