Triethylamine → HCID 15237344, compound

HRID 2226539Notes

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

Conditions

Temperature: 0 °C

Procedure

4,5-Diphenyl-2-oxazolyl-methylformamide (14 g, 0.05 mol) 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 (1 vol), extracted with dichloromethane, washed with saturated sodium carbonate solution, brine and dried (Na2SO4) to give 13 g (98%) of 27 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

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

Sources & evidence

ORD record: ord-8af888b182b34e42ba754c0be32b4aa4
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348969

Reaction notes

Loading…