1,5-Dibromopentane → HCID 54190112, compound

HRID 1018753Notes

Reaction equation

HRID 1018753 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH:15][S:16]([C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])(=[O:18])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br>CN(C=O)C>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[N:15]([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][Br:30])[S:16]([C:19]2[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])(=[O:17])=[O:18])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 54507950HCID 54507950, compound

Product 1

HCID 54190112HCID 54190112, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 450 mg (1.20 mmol) of N-(9-acridyl)-mesitylenesulfonamide in 20 mL of DMF was placed under an atmosphere of argon and cooled to 0° C. To the cooled solution was added 36 mg (1.42 mmol) of NaH (95%). The reaction mixture was stirred at 0° C. for 5 min and at room temperature for 1 hr. Then the reaction mixture was cooled to 0° C., and 1.65 mL (12.1 mmol) of 1,5-dibromopentane were added. The reaction mixture was stirred at 70-80° C. for 23 hr. The reaction mixture was cooled, and quenched with 20 mL of water. The mixture was partitioned between CH2Cl2 and water. The aqueous phase was washed with CH2Cl2 (2×20 mL). The CH2Cl2 washes were combined with the organic phase, dried with MgSO4, and evaporated to dryness. The material was purified by column chromatography on silica gel with CH2Cl2 to afford 382.2 mg (60%) of bromide 42 as an orange oil: 1H NMR (300 MHz, CDCl3, TMS) δ8.25 (d, J=9 Hz, 2H), 7.94 (d, J=9 Hz, 2H), 7.76 (t, J=8 Hz, 2H), 7.45 (t, J=8 Hz, 2H), 6.87 (s, 2H), 4.0-3.9 (m, 2H), 3.27 (t, J=6.5 Hz, 2H), 2.30 (s, 3H), 2.22 (s, 6H), 1.8-1.6 (m, 4H), 1.4-1.3 (m, 2H).

Workup

  1. temperatureThen the reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at 70-80° C. for 23 hr
  3. temperatureThe reaction mixture was cooled
  4. customquenched with 20 mL of water
  5. customThe mixture was partitioned between CH2Cl2 and water
  6. washThe aqueous phase was washed with CH2Cl2 (2×20 mL)
  7. dry with materialdried with MgSO4
  8. customevaporated to dryness
  9. customThe material was purified by column chromatography on silica gel with CH2Cl2

Sources & evidence

ORD record
ord-897dc4b16007463980845de23c2aa170
Source dataset
uspto-grants-2002_11
Patent number
US06482943B1

Reaction notes

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