Methanol → 3-(9-Phenylxanthen-9-yl)aminopropyne

HRID 849439Notes

Reaction equation

HRID 849439 reaction equation
Cl[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[NH2:22][CH2:23][C:24]#[CH:25].CO>CN(C=O)C>[C:16]1([C:2]2([NH:22][CH2:23][C:24]#[CH:25])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=3[O:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1706559-Chloro-9-phenyl-9H-xantheneHCID 239041Propargylamine

Product 1

HCID 100867933-(9-Phenylxanthen-9-yl)aminopropyneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Chloro-9-phenylxanthen (14.7 g, 50 mmol) was added in two equal portions over 0.5 h to a stirred solution of 3-aminopropyne (8.6 mL, 125 mmol) in DMF (100 mL). After 3 h, MeOH (20 mL) was added and the reaction mixture was stirred for 15 min. The mixture was then extracted into diethyl ether (500 mL) and washed with H2O (3×300 mL), dried (Na2SO4), and the solvent removed under vacuum. The resulting yellow oil was dried under high vacuum (4 h), and then redissolved in hot diethyl ether (70 mL). The solution was kept at -20° C. for 24 h and then filtered, the solid washed with ice-cold hexand (2×50 mL) followed by ice-cold diethyl ether (2×50 mL), giving 12 as a colourless powder (12.7 g, 82%), mp 116-8° C. 1H NMR (d6 -DMSO): δ2.86 (dd, 2H, H3, J=7.3, 4.4 Hz), 2.99 (t, 1H, H1, J=2.4 Hz), 4.01 (t, 1H, NH, J=7.2 Hz), 6.98-7.50 (m, 13H, Px CH). 13C NMR (d6 -DMSO): δ32.8 (C3), 59.7 (Px C9), 73.4 (C1), 82.7 (C2), 1160.0 and 123.5 (Px CH), 125.0 (Px C8a and C9a), 126.3, 126.4, 128.0, 128.6, 128.7 (Px CH), 149.5 (Px C1'), 150.7 (Px C4a and C10a). FABMS m/z 311 (M+). Anal. calcd for C22H17NO: C, 84.8; H, 5.51; N,4.50. Found: C, 84.4; H. 5.73; N, 4.30.

Workup

  1. extractionThe mixture was then extracted into diethyl ether (500 mL)
  2. washwashed with H2O (3×300 mL)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed under vacuum
  5. customThe resulting yellow oil was dried under high vacuum (4 h)
  6. dissolutionredissolved in hot diethyl ether (70 mL)
  7. waitThe solution was kept at -20° C. for 24 h
  8. filtrationfiltered
  9. washthe solid washed with ice-cold hexand (2×50 mL)

Sources & evidence

ORD record
ord-ce9726b62b0645b095f9d088eb09e359
Source dataset
uspto-grants-2000_01
Patent number
US06013434

Reaction notes

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