1-Bromopentane → HCID 19363411, compound

HRID 850472Notes

Reaction equation

HRID 850472 reaction equation
[NH2:1][C:2]1[C:3]([CH2:18][S:19][CH3:20])=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6].CC(C)([O-])C.[K+].Br[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CN(C=O)C>[CH3:17][O:16][C:15]1[CH:14]=[CH:13][C:4]([C:5]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6])=[C:3]([CH2:18][S:19][CH3:20])[C:2]=1[NH:1][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 19363473HCID 19363473, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19363411HCID 19363411, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Pentyl 3-amino-4-methoxy-2-methylthiomethylbenzoate (830 mg, 2.79 mmol) and DMF (4.0 ml) were mixed, and potassium t-butoxide (470 mg, 4.19 mmol) and bromopentane (0.62 ml, 5.0 mmol) were successively added to this solution. The mixture was stirred at 100° C. for 1 hour and filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=15/1) to give pentyl 4methoxy-2-methylthiomethyl-3-pentylaminobenzoate (178 mg, 17%) as a pale-yellow oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-b4d00e27bdd94096bf645c20a79edc33
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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