Trimethyl orthoformate → Benzooxazole-5-carboxylic Acid (1-propylbutyl)amide

HRID 339338

Reaction equation

HRID 339338 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1O)[C:17](O)=O.C(OC)(OC)OC>>[CH2:22]([CH:14]([NH:13][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[N:3][C:4]=2[CH:9]=1)=[O:12])[CH2:15][CH2:16][CH3:17])[CH2:21][CH3:20]

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformateHCID 650833-Amino-4-hydroxybenzoic acidHCID 190067671,3-Benzoxazole-5-carboxylic acid

Product 1

HCID 57527842Benzooxazole-5-carboxylic Acid (1-propylbutyl)amideYield 15%

Conditions

Temperature
65 °C

Procedure

benzooxazol-5-carboxylic acid: A mixture of 3-amino-4-hydroxybenzoic acid (500 mg, 3.26 mmol) and trimethyl orthoformate (5 mL) was heated at 65° C. for 2 h under argon. The reaction mixture was cooled to room temperature, filtered and washed with hexanes. The filtrate was concentrated in vacuo to afford the product as a white solid (78 mg, 15%): 1H NMR (500 MHz, CDCl3): δ 8.57 (d, J=1.5 Hz, 1H), 8.20 (dd, J=8.4, 1.8 Hz, 1H), 8.20 (s, 1H), 7.67 (d, J=9.0 Hz, 1H). MS (M+H, 164).

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-28e8382400904dea99a15adf851cb309
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Linked notes

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