Methanol → HCID 70590487, compound

HRID 1395505Notes

Reaction equation

HRID 1395505 reaction equation
[Br:1][CH2:2][C:3]1([CH3:30])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18]C(=O)CC3C=CC=CC=3)[C@H:5]2[S:4]1=[O:29].CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>C(Cl)Cl>[ClH:13].[Br:1][CH2:2][C:3]1([CH3:30])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH2:18])[C@H:5]2[S:4]1=[O:29]

Participants

6

Reactant 4

HCID 887MethanolHCID 949N,N-DimethylanilineHCID 24819Phosphorus pentachlorideHCID 70592298HCID 70592298, compound

Product 1

HCID 70590487HCID 70590487, compoundYield 146.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate-1-oxide (1.12 g) was dissolved in dried methylene chloride (10 ml). To this solution were added dimethyl aniline (0.36 g) under cooling at -15° C. and then phosphorus pentachloride (0.6 g), and the mixture was stirred for 3 hours. To the solution was added anhydrous methanol (0.7 g) under cooling at -40° C. and the solution was stirred for 2 hours and further stirred for 1 hour at -15° C. After the reaction, precipitated crystals were collected by filtration, washed with a small amount of methylene chloride and then dried to give 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-aminopenam-3-carboxylate-1-oxide hydrochloride (0.70 g), mp 147° to 154° C. (dec.).

Workup

  1. temperatureunder cooling at -40° C.
  2. stirringfurther stirred for 1 hour at -15° C
  3. customAfter the reaction
  4. customprecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed with a small amount of methylene chloride
  7. customdried

Sources & evidence

ORD record
ord-96f162636e9b4842b94ce6a2c8a5232f
Source dataset
uspto-grants-1980_05
Patent number
US04203897

Reaction notes

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