Butyl bromide → HCID 135609944, compound

HRID 2260460Notes

Reaction equation

HRID 2260460 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[OH:22])[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([S:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)[N:10]=1.C(=O)([O-])[O-].[K+].[K+].N1C=NC=NC=1.Br[CH2:49][CH2:50][CH2:51][CH3:52]>O.CN(C)C=O>[CH2:49]([O:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:7][CH2:2][CH2:3][CH3:4])=[CH:17][C:16]=3[OH:22])[N:12]=[C:11]([C:23]3[CH:28]=[CH:27][C:26]([S:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[N:10]=2)=[C:2]([OH:1])[CH:7]=1)[CH2:50][CH2:51][CH3:52]

Participants

7

Reactant 4

HCID 8002Butyl bromideHCID 92621,3,5-TriazineHCID 11430Potassium CarbonateHCID 135838255HCID 135838255, compound

Product 1

HCID 135609944HCID 135609944, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a 500 mL round bottomed flask equipped with a magnetic stirrer, condenser and nitrogen atmosphere are charged 2.0 g (4.2 mmol) of 2,4-bis-(2,4-dihydroxyphenyl)-6-[4-(phenylthio)phenyl]-s-triazine, 0.58 g (4.2 mmol) of potassium carbonate and 30 mL of N,N-dimethylformamide. The mixture is heated to 90° C., and the s-triazine compound dissolves readily. Bromobutane (4.5 mL, 42.0 mmol) is added all at once. The reaction mixture is heated at 90° C. for 2.5 hours and then stirred at room temperature overnight yielding a yellow precipitate. Chilled water is added and the yellow precipitate is isolated by vacuum filtration to give 2.74 g of crude product. The crude product is purified by flash chromatography with 1:1 heptane:ethyl acetate to afford 0.26 g (10%) yield of the title compound as a yellow solid; mp>250°.

Workup

  1. customTo a 500 mL round bottomed flask equipped with a magnetic stirrer, condenser
  2. temperatureThe reaction mixture is heated at 90° C. for 2.5 hours
  3. customyielding a yellow precipitate
  4. customthe yellow precipitate is isolated by vacuum filtration
  5. customto give 2.74 g of crude product
  6. customThe crude product is purified by flash chromatography with 1:1 heptane

Sources & evidence

ORD record
ord-772c83da69214f39be12384f9f82a647
Source dataset
uspto-grants-1995_12
Patent number
US05476937

Reaction notes

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