Methyl chloroformate → 5-Butyl-2-(4-isothiocyanatophenyl)pyrimidine

HRID 1111489Notes

Reaction equation

HRID 1111489 reaction equation
[CH2:1]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=S)[S-:19])=[CH:13][CH:12]=2)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].C([NH+](CC)CC)C.ClC(OC)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([C:5]1[CH:10]=[N:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[S:19])=[CH:13][CH:12]=2)=[N:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 22152660HCID 22152660, compound

Product 1

HCID 146189505-Butyl-2-(4-isothiocyanatophenyl)pyrimidineYield 81%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

6.77 g of triethylammonium p-(5-butyl-2-pyrimidinyl)-phenyldithiocarbamate were largely dissolved in 60 ml of chloroform and 2.5 ml of triethylamine. The mixture was subsequently treated dropwise with 2.00 ml of methyl chloroformate within 5 minutes while stirring and cooling with an ice bath The ice bath was removed after 10 minutes. After a further 60 minutes the yellowish solution was washed once with 20 ml of 0.5 N hydrochloric acid and three times with 20 ml of water each time, dried over sodium sulphate and concentrated. Chromatography of the residue on 60 g of silica gel with hexane/ethyl acetate (vol. 95:5) gave 3.65 g of p-(5-butyl-2-pyrimidinyl)phenyl isothiocyanate which was recrystallized twice from hexane for further purification. Yield 3.17 g; m.p. (C-S) 60.8° C., cl.p. (S-I) 77.8° C.

Workup

  1. customwas removed after 10 minutes
  2. washAfter a further 60 minutes the yellowish solution was washed once with 20 ml of 0.5 N hydrochloric acid and three times with 20 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4458cb105c28433b924a901f43cd704f
Source dataset
uspto-grants-1990_12
Patent number
US04980486

Reaction notes

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