Dichloromethane → HCID 178501988, compound

HRID 26440Notes

Reaction equation

HRID 26440 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 a 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 potassium carbonate and evaporated under reduced pressure. Recrystallization of the residue from methanol yields dimethyl 6-[3,6-dihydro-1(2H)-pyridyl]-2,4-pyrimidine-dicarbamate-3-oxide, having a melting point of 202°-203° C.

Workup

  1. stirringThe mixture is stirred a 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 potassium carbonate
  6. customevaporated under reduced pressure
  7. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-ed5ef941f10d47f5b77e3654f6dfb4b2
Source dataset
uspto-grants-1979_04
Patent number
US04150132

Reaction notes

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