Phosgene → HCID 19937149, compound

HRID 36601Notes

Reaction equation

HRID 36601 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7](=[O:28])[CH2:8][S:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]([N:19]2[CH2:23][CH:22]([O:24][CH3:25])[CH2:21][NH:20]2)=[S:18])[C:13]([F:26])=[CH:12][C:11]=1[Cl:27]>C1(C)C=CC=CC=1>[Cl:27][C:11]1[C:10]([S:9][CH2:8][C:7]([O:6][CH3:5])=[O:28])=[CH:15][C:14]([N:16]=[C:17]2[N:19]3[N:20]([CH2:21][CH:22]([O:24][CH3:25])[CH2:23]3)[C:1](=[O:2])[S:18]2)=[C:13]([F:26])[CH:12]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 54248137alpha-[2-Chloro-4-fluoro-5-(4-methoxypyrazolidinyl-thiocarbonylamino)-phenylthio]-acetic acid methyl ester

Product 1

HCID 19937149HCID 19937149, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
22 °C

Procedure

At 0°-5° C., 4.2 ml of phosgene solution in toluene (20%) are added to a solution of 2.8 g of α-[2-chloro-4-fluoro-5-(4-methoxypyrazolidinyl-thiocarbonylamino)-phenylthio]-acetic acid methyl ester in 20 ml of toluene. After stirring for 2 hours at 22° C., the organic phase is washed with water, dried and concentrated. The product is purified by means of column chromatography to yield 2.21 g of the desired product, 8-(4-chloro-2-fluoro-5-methoxy-carbonylmethylthio-phenylimino)-3-methoxy-7-thia-1,5-diazabicyclo[3.3.0]octan-6-one, in the form of a yellow oil.

Workup

  1. washthe organic phase is washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe product is purified by means of column chromatography

Sources & evidence

ORD record
ord-72a5c635871e46d0ab0545bfd31be5c3
Source dataset
uspto-grants-1995_05
Patent number
US05416065

Reaction notes

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