Dichloromethane → HCID 178501988, compound

HRID 27226Notes

Reaction equation

HRID 27226 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.[CH3:19][O:20][C:21](Cl)=[O:22]>C(N(CC)CC)C>[N:10]1([C:4]2[N:3]=[C:2]([NH:1][C:21]([O:20][CH3:19])=[O:22])[N+:7]([O-:8])=[C:6]([NH:9][C:21]([O:20][CH3:19])=[O:22])[CH:5]=2)[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 178507852HCID 178507852, compound

Product 1

HCID 178501988HCID 178501988, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

45 G. of 2,4-diamino-6-[3,6-dihydro-1(2H)-pyridyl]pyrimidine-3-oxide are mixed in 600 ml. of methylene chloride with 90 ml. of triethylamine and cooled to 5° C. 90 Ml. of chloroformic acid methyl ester are added dropwise while stirring. The mixture is stirred at 5° C. for 30 minutes and at room temperature for 18 hours. Then, the mixture is treated with 100 ml. of methanol and subsequently extracted with 400 ml. of methylene chloride, washed with water, dried over sodium sulfate and evaporated under reduced pressure. Recrystallization of the residue from methanol yields dimethyl 6-[3,6-dihydro-1(2H)-pyridyl]-2,4-pyrimidinedicarbamate-3-oxide having a melting point of 202°-203° C.

Workup

  1. stirringThe mixture is stirred at 5° C. for 30 minutes and at room temperature for 18 hours
  2. additionThen, the mixture is treated with 100 ml
  3. extractionof methanol and subsequently extracted with 400 ml
  4. washof methylene chloride, washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-e76883d0c9ab47119fa50fda1c020f78
Source dataset
uspto-grants-1980_09
Patent number
US04220772

Reaction notes

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