Ethyl formate → HCID 9841073, compound

HRID 1057613Notes

Reaction equation

HRID 1057613 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH2:24])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25](OCC)=[O:26]>>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH:24][CH:25]=[O:26])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 9839928HCID 9839928, compound

Product 1

HCID 9841073HCID 9841073, compoundYield 75%

Conditions

Temperature
67.5 °C

Procedure

A mixture of 2-[(9-benzyl-9H-carbazol-4-yl)oxy]ethylamine (0.0714 g, 0.226 mmol) and ethyl formate (3 mL) is stirred at 65-70° C. for 45 min. After cooling, excess ethyl formate is removed in vacuo and the residue is partitioned between CH2Cl2 and aq. sodium sulfate. The organic layers are dried over sodium sulfate and concentrated; the residue is crystallized from CH2Cl2-EtOAc-hexane to give 0.0585 g (75%) of the title compound as a white, crystalline solid; mp 161-162° C.; MS (ESI+) for m/z 345 (M+H)+, 367 (M+Na); 1H NMR (CDCl3) δ3.95, 4.38, 5.52, 6.13, 6.68, 7.03, 7.10, 7.2-7.4, 8.27, 8.29; IR (drift) 3297, 1659, 1459, 1385, 1341, 1332, 1269, 1255, 1145, 1116, 780, 747, 737, 717, 700 cm−1. Anal. Calcd for C22H20N2O2: C, 76.72; H, 5.85; N, 8.13. Found: C, 76.53; H, 5.99; N, 8.09.

Workup

  1. temperatureAfter cooling
  2. customexcess ethyl formate is removed in vacuo
  3. customthe residue is partitioned between CH2Cl2 and aq. sodium sulfate
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is crystallized from CH2Cl2-EtOAc-hexane

Sources & evidence

ORD record
ord-2a922e170e4c447197d232933b2365f0
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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