Dichloromethane → HCID 178452818, compound

HRID 26442Notes

Reaction equation

HRID 26442 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH2:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11]2)[N:3]=1.C(Cl)Cl.[CH2:19]([O:23][C:24](Cl)=[O:25])[CH:20]([CH3:22])[CH3:21]>C(N(CC)CC)C>[N:10]1([C:4]2[N:3]=[C:2]([NH:1][C:24]([O:23][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:25])[N+:7]([O-:8])=[C:6]([NH:9][C:24]([O:23][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:25])[CH:5]=2)[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 62365Isobutyl chloroformateHCID 178507852HCID 178507852, compound

Product 1

HCID 178452818HCID 178452818, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

20.7 G. of 2,4-diamino-6-[3,6-dihydro-1(2H)-pyridyl]pyrimidine-3-oxide are mixed with 250 ml. of methylene chloride and 35 ml. of triethylamine and cooled to 5° C. 40 Ml. of chloroformic acid isobutyl ester are added dropwise while stirring. After completion of the addition, the mixture is stirred at 5° C. for 15 minutes and then at room temperature for 2 hours. The solution is treated with 200 ml. of water and extracted with methylene chloride. The organic phase is evaporated and the residue is crystallized from ethanol. There is obtained diisobutyl 6-[3,6-dihydro-1(2H)-pyridyl]-2,4-pyrimidine-dicarbamate-3-oxide, having a melting point of 137°-139° C. (decomposition).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture is stirred at 5° C. for 15 minutes
  3. additionThe solution is treated with 200 ml
  4. extractionof water and extracted with methylene chloride
  5. customThe organic phase is evaporated
  6. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-fb73eda637ff4092b4f130083da7a559
Source dataset
uspto-grants-1979_04
Patent number
US04150132

Reaction notes

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