반응 #2476691

반응 방정식

water

4-fluoro-3-nitrobenzotrifluoride

glycine tert-butyl ester hydrochloride

NaHCO3

→

title compound

수율 79.3%

tert-Butyl (2-nitro-4-trifluoromethyl-phenylamino)-acetate

수율 79.3%

용매

DMSO

반응 조건

후처리

1. 1
   온도a further heating at 85° C. to 100° C. for 3 h
2. 2
   온도The reaction is then cooled to rt
3. 3
   기타The yellow to orange solid formed
4. 4
   여과is filtered over a fritted funnel
5. 5
   세척rinsed thoroughly with water
6. 6
   기타dried under high vacuum

실험 절차

A mixture of 4-fluoro-3-nitrobenzotrifluoride (209 mg, 1 mmol), glycine tert-butyl ester hydrochloride (201 mg, 1.2 mmol) and NaHCO3 (128 mg, 2 mmol) in dry DMSO (1 ml) is stirred overnight at 50 or 65° C. In case the reaction is not complete a further heating at 85° C. to 100° C. for 3 h is necessary. The reaction is then cooled to rt and water is added. The yellow to orange solid formed is filtered over a fritted funnel, rinsed thoroughly with water and dried under high vacuum. This yields the title compound (254 mg) in 79% as a yellow solid: tR=1.08 min (LC-3), ESI-MS (pos.): m/z 403.2 [M+2AcCN]+, m/z 321.56 [M+H]+, 1H-NMR (DMSO-d6): δ (ppm) 1.44 (s, 9H, tBu), 4.23 (d, 2H, NHCH2CO2), 7.08 (d, 1H, Harom), 7.80 (dd, 1H, H, m), 8.34 (br. s, 1H, Harom), 8.65 (t, 1H, NH).

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