Phosgene → HCID 18649518, compound

HRID 1646455Notes

Reaction equation

HRID 1646455 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]([C:9]1([S:13][C:14]2[CH:19]=[C:18]([NH:20][C:21]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]3)=[S:22])[C:17]([F:29])=[CH:16][C:15]=2[Cl:30])[CH2:12][CH2:11][CH2:10]1)=[O:8].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:30][C:15]1[C:14]([S:13][C:9]2([C:7]([O:6][CH3:5])=[O:8])[CH2:12][CH2:11][CH2:10]2)=[CH:19][C:18]([N:20]=[C:21]2[N:23]3[N:24]([CH2:25][CH2:26][CH2:27][CH2:28]3)[C:1](=[O:2])[S:22]2)=[C:17]([F:29])[CH:16]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 86746491HCID 86746491, compound

Product 1

HCID 18649518HCID 18649518, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

While stirring at a temperature of +10° C., 12.5 ml of a 20% solution of phosgene in toluene are added dropwise to a solution of 10.4 g of 1-[2-chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclobutanecarboxylic acid methyl ester and 10 ml of triethylamine in 100 ml of toluene. The reaction mixture is then stirred for 6 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 4.6 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclobutylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7one, ηD22 1.6010.

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 4.6 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclobutylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7one, ηD22 1.6010

Sources & evidence

ORD record
ord-f99417fb346a47eeb0b1a7d990f00a74
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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