Triphenylphosphine → HCID 86639523, compound

HRID 1022402Notes

Reaction equation

HRID 1022402 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N=C=NC(C)C)(C)C.[Cl:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[C:35]([NH:40][CH2:41][CH2:42]O)[N:34]=[C:33]2[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[C:50]([OH:53])(=[S:52])[CH3:51].C(=O)(O)[O-].[Na+]>C1COCC1.C1(C)C=CC=CC=1.O>[C:50]([S:52][CH2:42][CH2:41][NH:40][C:35]1[N:34]=[C:33]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:32]2[C:37](=[CH:38][CH:39]=[C:30]([Cl:29])[CH:31]=2)[N:36]=1)(=[O:53])[CH3:51]

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 12734DiisopropylcarbodiimideHCID 516892Sodium BicarbonateHCID 1912855HCID 1912855, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86639523HCID 86639523, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 292 mg of triphenylphosphine in dehydrated THF (3 ml) was added dropwise 563 mg of a 40% solution of diisopropylcarbodiimide in toluene under ice cooling, followed by stirring for 20 minutes. To the resulting suspension was added dropwise a solution of 167 mg of 6-chloro-2-(2-hydroxyethylamino)-4-phenylquinazoline (compound No. Ic3-1) in dehydrated THF (2 ml) under ice cooling, and immediately 127 mg of thioacetic acid was added dropwise. The resulting yellow clear solution was stirred for 1 hour under ice cooling, stirred at room temperature for 1 hour, poured into a saturated solution of sodium bicarbonate in water, and then extracted with chloroform. The extract was concentrated. The resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1) to obtain 170 mg of the titled compound. Mp.128.9° C. 1H NMR (CDCl3): 2.34 (3H, s), 3.22 (2H, t, J=6.5 Hz), 3.73 (2H, q, J=6.5 Hz), 5.74 (1H, br. t, J=6.5 Hz), 7.53-7.62 (5H, m), 7.65-7.70 (2H, m), 7.77 (1H, s).

Workup

  1. stirringThe resulting yellow clear solution was stirred for 1 hour under ice cooling
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted with chloroform
  4. concentrationThe extract was concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d872175e166348018bc7cff7c785a4aa
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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