Triethylamine → HCID 15237344, compound

HRID 1656417Notes

Reaction equation

HRID 1656417 reaction equation
[C:1]1([C:7]2[N:8]=[C:9](N(C)C=O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:33]([N:35](CC)[CH2:36]C)C>ClCCl.O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:36][N+:35]#[C-:33])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 57152568HCID 57152568, compound

Product 1

HCID 15237344HCID 15237344, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4,5-Diphenyl-2-oxazolyl-methylformamide (14 g, 0.05mol) was dissolved in dichloromethane (70 mL) /triethylamine (16 mL) and cooled to about 0° C. under N2. Upon dropwise addition of phosphorous oxychloride (4.7 mL, 0.05 mol), the reaction mixture was warmed to about 25° C. and stirred about 1 hour. A 40% sodium carbonate solution (50 mL) was added and after about 15 minutes the reaction mixture was diluted with water (Ivol), extracted with dichloromethane, washed with saturated sodium carbonate solution, brine and dried (Na2SO4) to give 13 g (98%) of 4 as a white solid. Recrystallization from ether gave light amber colored crystals, mp 95°-96° C. IR KBr, cm-1) 2970, 2956, 2160 (NC), 1604, 1594, 1502, 1446, 1338, 1212, 1054, 1026, 954, 916, 778, 764, 712, 694, 674, 654, 526. 1H NMR (300 MHz, CDCl3)δ 4.81 (2H, s), 7.31 to 7.41 (7H, m),7.57 to 7.66 (5H, m). 13C NMR (75 MHz, CDCl3) ppm 39.03, 126.78, 127.86, 128.04, 128.58, 128.73, 128.83, 129.25, 131.53, 135.77, 147.28, 153.17, 160.84. m/e 261 (MH+).

Workup

  1. temperaturethe reaction mixture was warmed to about 25° C.
  2. extractionextracted with dichloromethane
  3. washwashed with saturated sodium carbonate solution, brine
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-c2581e98015f43aaac541191f0c6a692
Source dataset
uspto-grants-1993_10
Patent number
US05254576

Reaction notes

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