Trimethyl orthoacetate → HCID 57527791, compound

HRID 339339

Reaction equation

HRID 339339 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][C:5]=2[N:6]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1O)[C:18](O)=O.C(OC)(OC)(OC)C>>[CH2:23]([CH:15]([NH:14][C:11]([C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1)=[O:13])[CH2:16][CH2:17][CH3:18])[CH2:22][CH3:21]

Participants

4

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 650833-Amino-4-hydroxybenzoic acidHCID 232822842-Methyl-1,3-benzoxazole-5-carboxylic acid

Product 1

HCID 57527791HCID 57527791, compoundYield 80%

Conditions

Temperature
65 °C

Procedure

2-methyl benzooxazol-5-carboxylic acid: A mixture of 3-amino-4-hydroxybenzoic acid (1.5 g, 9.79 mmol) and trimethyl orthoacetate (15 mL, large excess) was heated at 65° C. for 5 hrs under argon. The reaction mixture was cooled to room temperature, filtered, washed with hexanes. The filtrate was concentrated in vacuo to afford the product as a yellow solid (1.4 g, 80%): 1H NMR (500 MHz, CD3OD) δ 8.26 (d, J=1.7 Hz, 1H), 8.07 (dd, J=8.5, 1.6 Hz, 1H), 7.67 (d, J=8.2 Hz, 1H), 2.67 (s, 1H); MS (APCI, M+1): 178.10.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with hexanes
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-77586c13ce834404bfd10b1312d178a8
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Linked notes

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