Triethyl orthoacetate → HCID 59560314, compound

HRID 1643817Notes

Reaction equation

HRID 1643817 reaction equation
[C:1](OCC)(OCC)(OCC)[CH3:2].Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([OH:25])[C:23]=1[OH:24])[C:17]([O:19][CH3:20])=[O:18]>CCCCCC>[OH:25][C:22]1[C:23]2[O:24][C:1]([CH3:2])=[N:13][C:14]=2[CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:21]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 44203162HCID 44203162, compound

Product 1

HCID 59560314HCID 59560314, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To stirred triethyl orthoacetate (35.0 mL, 190 mmol) was added methyl 3-amino-4,5-dihydroxybenzoate hydrochloride (6.00 g, 27.3 mmol). The stirred suspension was refluxed for 20 min and cooled to room temperature. The reaction mixture was poured into hexane (200 mL). The formed precipitate was separated by filtration and vacuum-dried to afford the desired benzoxazole (4.98 g, 24.04 mmol, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.74 (br. s, 1H), 7.66 (d, J=1.4 Hz, 1H), 7.43 (d, J=1.4 Hz, 1H), 3.85 (s, 3H), 2.62 (s, 3H).

Workup

  1. temperatureThe stirred suspension was refluxed for 20 min
  2. customThe formed precipitate was separated by filtration
  3. customvacuum-dried

Sources & evidence

ORD record
ord-b55e28ced234475bb8e4af33ee0e1022
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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