2,6-Lutidine → HCID 17463116, compound

HRID 1034403Notes

Reaction equation

HRID 1034403 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.N1C(C)=CC=CC=1C.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26]>O1CCCC1>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1)=[O:26]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 682422-Furancarbonyl chlorideHCID 7379202-Methyl-1,3-benzoxazol-5-amine

Product 1

HCID 17463116HCID 17463116, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
3 °C

Procedure

5-Amino-2-methylbenzoxazole (14 8 g, 0.100 mol) and 2,6-lutidine (12.0 g, 0.111 mol) were combined with 100 mL of tetrahydrofuran (THF) and the solution was cooled to 3° C. in an ice-bath under nitrogen. 2-Furoyl chloride (13.7 g, 0.105 mol) in 20 mL of THF was added dropwise so as to keep the temperature below 10° C. After addition the ice-bath was removed and after stirring for 1 hour the mixture was poured into 300 mL of water. The solid was collected and washed with water and dried. This afforded 21.1 g (87% yield) of product; m.p. 156°-158° C.

Workup

  1. customthe temperature below 10° C
  2. customwas removed
  3. additionwas poured into 300 mL of water
  4. customThe solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9e31afdb253d49f0994bd820926d7d3a
Source dataset
uspto-grants-1994_05
Patent number
US05316904

Reaction notes

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