Dichloromethane → Carprazidil

HRID 127675Notes

Reaction equation

HRID 127675 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:4]([N:14]2[CH2:19][CH:18]=[CH:17][CH2:16][CH2:15]2)[N:3]=1.C(Cl)Cl.[C:23](Cl)(Cl)=[O:24].[OH-].[Na+]>C1(C)C=CC=CC=1.O.C(N(CC)CC)C>[N:14]1([C:4]2[CH:5]=[C:6]([NH:9][C:10]([O:12][CH3:13])=[O:11])[N:7]3[O:8][C:23](=[O:24])[N:1]=[C:2]3[N:3]=2)[CH2:15][CH:16]=[CH:17][CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 178501990HCID 178501990, compound

Product 1

HCID 68875Carprazidil

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

53 Mg. of methyl 2-amino-6-[3,6-dihydro-1(2H)-pyridyl]-4-pyrimidinecarbamate-3-oxide are dissolved in 5 ml. of methylene chloride. The solution is cooled to 0° C. and treated with 0.2 ml. of triethylamine and 0.12 ml. of 20% phosgene in toluene. The mixture is stirred for 30 minutes and then treated with 0.5 ml. of concentrated sodium hydroxide and 10 ml. of water. After stirring for 15 minutes, the two phases are separated, and the organic phase is again washed with water. The combined aqueous phases are acidified with hydrochloric acid, there being obtained pure methyl 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 213°-214° C.

Workup

  1. additiontreated with 0.2 ml
  2. additiontreated with 0.5 ml
  3. stirringAfter stirring for 15 minutes
  4. customthe two phases are separated
  5. washthe organic phase is again washed with water

Sources & evidence

ORD record
ord-8b20909f724043b39a3deba6498ac48c
Source dataset
uspto-grants-1981_03
Patent number
US04256886

Reaction notes

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