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

HRID 2073128Notes

Reaction equation

HRID 2073128 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 0.5N 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. temperaturecooling with an ice bath
  2. customThe ice bath was removed after 10 minutes
  3. washAfter a further 60 minutes the yellowish solution was washed once with 20 ml of 0.5N hydrochloric acid and three times with 20 ml of water each time
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8044d42b70e94eb986cc1270ff4db333
Source dataset
uspto-grants-1990_04
Patent number
US04915480

Reaction notes

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