4-Methyloxybenzyl chloride → HCID 59610063, compound

HRID 1889183Notes

Reaction equation

HRID 1889183 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10]([Br:13])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[N:7]([C:8]1[S:9][C:10]([Br:13])=[CH:11][N:12]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 21300388tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

Product 1

HCID 59610063HCID 59610063, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a single necked round bottom flask (5-Bromo-thiazol-2-yl)-carbamic acid tert-butyl ester (1.4 g, 5.01 mmol) was dissolved in 25 ml dry DCM. To it 1,8-Diazabicyclo[5.4.0]undec-7-ene(DBU) (2.24 ml, 15.03 mmol) was added followed by 1-Chloromethyl-4-methoxy-benzene (1.02 ml, 7.52 mmol) addition was done and reaction mixture was stirred for overnight. Reaction was quenched by addition of water (20 ml), extracted with DCM (25 ml), Organic layer was separated and washed with brine (30 ml) and dried over anhydrous sodium sulfate, sodium sulfate was filtered and washed with DCM (20 ml) and solvent was evaporated on rotavapour to get required product. The crude material was purified by silica-gel column chromatography, eluting with 4% acetone in hexane. (1.4 g).

Workup

  1. customreaction mixture
  2. customReaction
  3. customwas quenched by addition of water (20 ml)
  4. extractionextracted with DCM (25 ml), Organic layer
  5. customwas separated
  6. washwashed with brine (30 ml)
  7. dry with materialdried over anhydrous sodium sulfate, sodium sulfate
  8. filtrationwas filtered
  9. washwashed with DCM (20 ml) and solvent
  10. customwas evaporated on rotavapour

Sources & evidence

ORD record
ord-5ecb4a5a5f2b471eaed0aaed490c6fa7
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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