Hexane → HCID 66920555, compound

HRID 1880438Notes

Reaction equation

HRID 1880438 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(OCC)(OCC)[CH3:2].Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([OH:24])[C:22]=1[OH:23])[C:17]([OH:19])=[O:18].[CH3:25]CCCCC>>[CH3:25][O:18][C:17]([C:16]1[CH:20]=[C:21]([OH:24])[C:22]2[O:23][C:1]([CH3:2])=[N:13][C:14]=2[CH:15]=1)=[O:19].[O:9]1[C:10]2[CH:11]=[CH:20][CH:21]=[CH:22][C:14]=2[N:13]=[CH:1]1

Participants

4

Reactant 3

HCID 8058HexaneHCID 66221Triethyl orthoacetateHCID 66920537HCID 66920537, compound

Product 1

HCID 66920555HCID 66920555, compoundYield 88%

Procedure

To stirred triethyl orthoacetate (35.0 mL, 190 mmol), 3-amino-4,5-dihydroxybenzoate hydrochloride (6.00 g, 27.3 mmol) was added. The stirred suspension was refluxed for 20 minutes 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 benzoxazole methyl 7-hydroxy-2-methyl-1,3-benzoxazole-5-carboxylate (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. additionwas added
  2. temperatureThe stirred suspension was refluxed for 20 minutes
  3. customThe formed precipitate was separated by filtration
  4. customvacuum-dried

Sources & evidence

ORD record
ord-7442f3b0ae1d4c74aa0330b9631d3cbd
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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