Ethyl orthoformate → HCID 59560280, compound

HRID 1177342Notes

Reaction equation

HRID 1177342 reaction equation
[CH:1](OCC)(OCC)OCC.Cl.[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([OH:24])[C:22]=1[OH:23])[C:16]([O:18][CH3:19])=[O:17]>CCCCCC>[OH:24][C:21]1[C:22]2[O:23][CH:1]=[N:12][C:13]=2[CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:20]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 44203162HCID 44203162, compound

Product 1

HCID 59560280HCID 59560280, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To stirred triethyl orthoformate (35.0 mL, 210 mmol) was added methyl 3-amino-4,5-dihydroxybenzoate hydrochloride (6.30 g, 28.7 mmol). The stirred suspension was refluxed for 20 min (until a clear solution formed), cooled to room temperature, and poured into hexane (200 mL). The formed precipitate was separated by filtration and vacuum-dried to afford the desired benzoxazole (4.26 g, 22.05 mmol, 77% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.90 (br. s, 1H), 8.79 (s, 1H), 7.80 (d, J=1.3 Hz, 1H), 7.50 (d, J=1.3 Hz, 1H), 3.86 (s, 3H).

Workup

  1. temperatureThe stirred suspension was refluxed for 20 min (until a clear solution
  2. customformed),
  3. customThe formed precipitate was separated by filtration
  4. customvacuum-dried

Sources & evidence

ORD record
ord-9692c4c45d364fa59540e00d2fdbdb30
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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