Methyl 2-methylbenzo[d]oxazole-6-carboxylate

Base Information

• Chemical Name: Methyl 2-methylbenzo[d]oxazole-6-carboxylate
• CAS No.: 136663-23-5
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60478781
• Nikkaji Number: J2.133.182A
• Wikidata: Q82312376
• Mol file: 136663-23-5.mol

Synonyms:136663-23-5;Methyl 2-methylbenzo[d]oxazole-6-carboxylate;Methyl 2-methyl-1,3-benzoxazole-6-carboxylate;Methyl 2-Methylbenzoxazole-6-carboxylate;6-Benzoxazolecarboxylic acid, 2-methyl-, methyl ester;MFCD00113064;Methyl2-methylbenzo[d]oxazole-6-carboxylate;2-methyl-benzooxazole-6-carboxylic acid methyl ester;SCHEMBL1680291;DTXSID60478781;CIGMBXJEQUHKPR-UHFFFAOYSA-N;methyl 2-methylbenzoxazole-6 carboxylate;SY108684;CS-0063936;FT-0723559;A849447;2-Methyl-benzoxazole-6-carboxylic acid methyl ester

Chemical Property of Methyl 2-methylbenzo[d]oxazole-6-carboxylate

Chemical Property:

• PSA: 52.33000
• LogP: 1.92280
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

NLT 98% ^*data from raw suppliers

Methyl2-Methylbenzo[d]oxazole-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(O1)C=C(C=C2)C(=O)OC
• Uses: Methyl 2-Methylbenzo[d]oxazole-6-carboxylate is a reactant that is useful for the synthesis of SB-?334867 (I) analogs. SB-?334867 is an orexin antagonist.

Technology Process of Methyl 2-methylbenzo[d]oxazole-6-carboxylate

There total 9 articles about Methyl 2-methylbenzo[d]oxazole-6-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Trimethyl orthoacetate (1445-45-0) + 3-hydroxy-4-aminobenzoic acid methyl ester (63435-16-5) → methyl 2-methyl-1,3-benzoxazole-6-carboxylate (136663-23-5)

Guidance literature:

Trimethyl orthoacetate; 3-hydroxy-4-aminobenzoic acid methyl ester; With trifluoroacetic acid; at 20 ℃; for 1.5h;

With sodium hydrogencarbonate; In dichloromethane; water;

Reference yield: 99.0%

dimethyl acetimidate hydrochloride + 3-hydroxy-4-aminobenzoic acid methyl ester (63435-16-5) → methyl 2-methyl-1,3-benzoxazole-6-carboxylate (136663-23-5)

Guidance literature:

In methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2012.08.109

Reference yield: 80.4%

acetyl chloride (75-36-5) + 3-hydroxy-4-aminobenzoic acid methyl ester (63435-16-5) → methyl 2-methyl-1,3-benzoxazole-6-carboxylate (136663-23-5)

Guidance literature:

With pyridinium p-toluenesulfonate; triethylamine; In xylene; for 8.5h; Heating / reflux;

upstream raw materials:

methyl 4-acetamido-3-hydroxybenzoate

methyl 3-hydroxy-4-nitrobenzoate

N,N-diethylaniline

3-hydroxy-4-aminobenzoic acid methyl ester

Downstream raw materials:

2-methyl-6-benzoxazole carboxylic acid

(2-methyl-1,3-benzoxazol-6-yl)methanol

1-(2-methylbenzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea

2-methyl-1,3-benzoxazole-6-carbaldehyde

Refernces

• 1、 Perrey, David A.,Gilmour, Brian P.,Runyon, Scott P.,Thomas, Brian F.,Zhang, Yanan. "Diaryl urea analogues of SB-334867 as orexin-1 receptor antagonists". scheme or table. p. 2980 - 2985. Retrieved 2011/06/24.
• 2、 -. "BENZAMIDE DERIVATIVES AS INHIBITORS OF HISTONE DEACETYLASE". Page/Page column 108. . Retrieved 2008/06/13.