Ethanol → HCID 86649468, compound

HRID 2190921Notes

Reaction equation

HRID 2190921 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:25](O)[CH3:26]>>[CH2:25]([O:18][C:17](=[O:19])[CH2:16][NH:15][C:13]([C:7]1[C:8](=[O:12])[O:9][C:10]2[C:5]([C:6]=1[OH:20])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2)=[O:14])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 54735959HCID 54735959, compound

Product 1

HCID 86649468HCID 86649468, compound

Procedure

A mixture of [(7-bromo-4-hydroxy-2-oxo-2H-chromene-3-carbonyl)-amino]-acetic acid (3.209 g, 9.38 mmol) and thionyl chloride (2.05 mL, 28.1 mmol) in ethanol (75 mL) was refluxed for 2 h; then cooled, the precipitates were collected via filtration and washed with cold ethanol, air dried to give the desired product (3.153 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=17.5 (s, 1H), 9.5 (br, 1H), 7.88 (dd, 1H, J=0.6 Hz, 8.4 Hz), 7.5-7.2 (m, 2H), 4.32-4.18 (m, 4H), 1.32 (t, 3H, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethen cooled
  3. filtrationthe precipitates were collected via filtration
  4. washwashed with cold ethanol, air
  5. customdried

Sources & evidence

ORD record
ord-fa1a54a64f214c21a6c259ab8db94fd2
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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