Dichloromethane → HCID 21904822, compound

HRID 1246950Notes

Reaction equation

HRID 1246950 reaction equation
[CH:1]1[C:14]2[CH:13]3[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)[CH2:7][N:6]3[CH2:15][CH2:16][N:17](C(OCC4C=CC=CC=4)=O)[CH2:18][C:4]([C:5]=23)=[CH:3][CH:2]=1.FC(F)(F)S(O)(=O)=O.C1(OC)C=CC=CC=1.[OH-].[Na+].C(Cl)[Cl:48]>O>[ClH:48].[CH:1]1[C:14]2[CH:13]3[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)[CH2:7][N:6]3[CH2:15][CH2:16][NH:17][CH2:18][C:4]([C:5]=23)=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6344Dichloromethane2×HCID 7519AnisoleHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acid2×HCID 10309319HCID 10309319, compound

Product 1

HCID 21904822HCID 21904822, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound from Example 5 (0.200 g, 0.53 mmol) was dissolved in methylene chloride (0.5 mL). Trifluoromethane sulfonic acid (0.0.329 mL, 3.72 mmol) and anisole (0.115 mL, 1.06 mmol) were added at 0° C. After 2 hours, another portion of trifluoromethane sulfonic acid (2 eq.) was added. After a total of 4 hours, the reaction was completed. 1 N NaOH was added to quench the reaction (pH=9–10). The contents of the flask were transferred to a separatory funnel with methylene chloride and water, and extracted with methylene chloride (3×). The combined organic extracts were dried with magnesium sulfate, filtered and concentrated to give a brown oil, crude desired product. Further purification (10% ammonia in 2M solution of methanol/ethyl acetate) yielded 0.067 g of desired product (52%). The free amine product (0.0605 g, 0.249 mmol) was then dissolved in diethyl ether, and a 2M solution of hydrogen chloride (0.137 mL, 0.274 mmol) was added. After 40 minutes, the yellow precipitate was filtered off to give the desired product.

Workup

  1. customAfter a total of 4 hours
  2. customto quench
  3. customthe reaction (pH=9–10)
  4. extractionextracted with methylene chloride (3×)
  5. dry with materialThe combined organic extracts were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil, crude desired product
  9. customFurther purification (10% ammonia in 2M solution of methanol/ethyl acetate)

Sources & evidence

ORD record
ord-cd31e03df3144d669ed0e7425ec4465a
Source dataset
uspto-grants-2006_10
Patent number
US07129237B2

Reaction notes

Loading…