Hydrochloric Acid → HCID 12970145, compound

HRID 722834Notes

Reaction equation

HRID 722834 reaction equation
CSC.B.[N+:5]([CH2:8][C:9]1([CH2:15][C:16]#[N:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([O-:7])=[O:6].CO.Cl>C1(C)C=CC=CC=1.O1CCOCC1>[N+:5]([CH2:8][C:9]1([CH2:15][CH2:16][NH2:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11275397HCID 11275397, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 12970145HCID 12970145, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Borane methyl sulphide (2.0 M in toluene, 1.3 mL, 2.6 mmol) was added to compound 3 (0.4 g, 2.2 mmol) in toluene (10 mL) under nitrogen. After heating to 60° C. for 3 hours, the mixture was allowed to cool, and 15 mL methanol was added followed by 15 mL 4 M HCl in dioxane. After reflux for 1 hour, the mixture was evaporated to dryness. Crystallization from ethyl acetate gave the required product as colorless crystals (0.23 g, 47%); mp 170–173° C.

Workup

  1. temperatureto cool
  2. temperatureAfter reflux for 1 hour
  3. customthe mixture was evaporated to dryness
  4. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-edd163ac620b406da8b2503b81382f57
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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