Hydrochloric Acid → HCID 12824304, compound

HRID 127682Notes

Reaction equation

HRID 127682 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])[CH:5]=[C:4]([N:17]2[CH2:22][CH:21]=[CH:20][CH2:19][CH2:18]2)[N:3]=1.C(Cl)(Cl)Cl.[C:27](Cl)(Cl)=[O:28].Cl>C1(C)C=CC=CC=1.C(N(CC)CC)C>[N:17]1([C:4]2[CH:5]=[C:6]([NH:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])[N:7]3[O:8][C:27](=[O:28])[N:1]=[C:2]3[N:3]=2)[CH2:18][CH:19]=[CH:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 6371PhosgeneHCID 178496342HCID 178496342, compound

Product 1

HCID 12824304HCID 12824304, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

2 G. of 2-methoxyethyl 2-amino-6-[3,6-dihydro-1(2H)-pyridyl]-4-pyrimidinecarbamate-3-oxide are dissolved at 0° C. in 15 ml. of chloroform and 3.7 ml. of triethylamine. The cold stirred mixture is treated with 3.2 ml. of 20% phosgene in toluene. The mixture is then stirred for 4 hours, acidified with hydrochloric acid, washed with water and extracted with methylene chloride. The organic phase is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The residue obtained is crystallized from methylene chloride and ether, there being obtained pure 2-methoxyethyl 5-[3,6-dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-pyrimidine-7-carbamate having a melting point of 195°-196° C.

Workup

  1. additionis treated with 3.2 ml
  2. stirringThe mixture is then stirred for 4 hours
  3. washwashed with water
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe residue obtained
  8. customis crystallized from methylene chloride and ether, there

Sources & evidence

ORD record
ord-5c0d79b2eed74106a92e5ec4ead8866e
Source dataset
uspto-grants-1981_03
Patent number
US04256886

Reaction notes

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