2,6-Lutidine → HCID 18961634, compound

HRID 1707554Notes

Reaction equation

HRID 1707554 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.[C:20]([O:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27])(=[O:22])[CH3:21]>O1CCCC1>[C:20]([O:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([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:27])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 796682-Acetoxybenzoyl chloride2×HCID 7379202-Methyl-1,3-benzoxazol-5-amine

Product 1

HCID 18961634HCID 18961634, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
3 °C

Procedure

5-Amino-2-methylbenzoxazole (18.6 g, 0.126 mol) and 2,6-lutidine (14.8 g, 0.138 mol) were combined with 125 mL of tetrahydrofuran and the solution was cooled to 3° C. in an ice-bath under nitrogen. 2-Acetoxybenzoyl chloride (25.0 g, 0.126 mol) was added as a solid, portionwise, so as to keep the temperature below 10° C. An additional 150 mL of tetrahydrofuran was added. After addition of all the 2-acetoxybenzoyl chloride, the ice-bath was removed and after stirring for 2 hr the mixture was poured into 300 mL of water and then combined with an additional 300 mL of water. The solid was collected and washed with water and dried. This afforded 33.6 g (86% yield) of product; m.p. 169°-171° C.

Workup

  1. customthe temperature below 10° C
  2. customthe ice-bath was 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-b31461a9b8ae42a694fa8c4f37f528ab
Source dataset
uspto-grants-1994_10
Patent number
US05354651

Reaction notes

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