Phosgene → 9-[4-Chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

HRID 1646469Notes

Reaction equation

HRID 1646469 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]([C:9]1([S:12][C:13]2[CH:18]=[C:17]([NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][NH:23]3)=[S:21])[C:16]([F:28])=[CH:15][C:14]=2[Cl:29])[CH2:11][CH2:10]1)=[O:8].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:29][C:14]1[C:13]([S:12][C:9]2([C:7]([O:6][CH3:5])=[O:8])[CH2:10][CH2:11]2)=[CH:18][C:17]([N:19]=[C:20]2[N:22]3[N:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[C:1](=[O:2])[S:21]2)=[C:16]([F:28])[CH:15]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 867464931-[2-Chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 198006209-[4-Chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

While stirring at a temperature of from 0° to +10° C., 5.7 ml of a 20% solution of phosgene in toluene are added dropwise to a solution of 3.7 g of 1-[2-chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester and 4.6 ml of triethylamine in 100 ml of toluene. The reaction mixture is then stirred for 4 hours and then introduced into ice-water. The organic phase is then separated off and dried over sodium sulfate. Concentration by evaporation and subsequent chromatographic purification by means of silica gel chromatography yield 3.7 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one, having a melting point of +149° C.

Workup

  1. customThe organic phase is then separated off
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration
  4. customby evaporation and subsequent chromatographic purification by means of silica gel chromatography yield 3.7 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

Sources & evidence

ORD record
ord-3e018f474b884c0da0559971f8a5f6f6
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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