Phosgene → N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1607229Notes

Reaction equation

HRID 1607229 reaction equation
C(Cl)(Cl)=O.Cl.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:19]([O:21][CH3:22])=[O:20])([CH3:18])[CH2:16][NH:15][N:14]=2)=[CH:9][CH:8]=1.[C:23](Cl)(=[O:25])[NH2:24].N[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1>C(OCC)(=O)C.C(N(CC)CC)C.C(#N)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([NH:24][C:23]([N:15]2[CH2:16][C:17]([C:19]([O:21][CH3:22])=[O:20])([CH3:18])[C:13]([C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)=[N:14]2)=[O:25])=[N:29][CH:30]=1

Participants

8

Reactant 4

HCID 6371PhosgeneHCID 661742-Amino-5-chloropyridineHCID 68048Carbamic chlorideHCID 198521223-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride

Product 1

HCID 19852657N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 10 ml of acetonitrile containing 4.5 ml of 2.5M phosgene in ethyl acetate was added a slurry of 2.9 g (10 mmole) of 3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride 2.0 g (20 mmole) of triethylamine and 20 ml of acetonitrile. After stirring for 10 minutes the carbamoyl chloride was judged to have been formed and then 1.5 g (11 mmole) of 2-amino-5-chloropyridine was added with an additional 2 g of triethylamine. After stirring for 18 hours the mixture was partitioned between ether and water, washed with brine, dried over magnesium sulfate, filtered concentrated, and chromatographed yielding N-(5-chloropyrid-2-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, mp 130°-146° C. NMR data was consistent with the structure.

Workup

  1. customto have been formed
  2. customwas partitioned between ether and water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-0dbb9f569893467689776ebb88e09f1d
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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