Triethylamine → HCID 178433411, compound

HRID 1271213Notes

Reaction equation

HRID 1271213 reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].[NH2:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O>CO>[CH2:19]([O:18][C:16]1[CH:17]=[C:9]2[C:10]([C:11](=[O:13])[N:3]=[C:1]([CH3:2])[NH:8]2)=[CH:14][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 235458842-Amino-4-(benzyloxy)benzoic acid

Product 1

HCID 178433411HCID 178433411, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.695 g (5.62 mmol) of ethyl acetoamidate hydrochloride in MeOH (16 ml) were added under stirring at RT 0.82 ml (5.86 mmol) of triethyl amine and 5 minutes later 1.14 g (4.69 mmol) of 2-amino-4-benzyloxy-benzoic acid. The reaction mixture was heated at reflux for 5 h, cooled to RT, the precipitate that had formed was filtered off by suction and dried in a high vacuum to give 0.9 g (69.4%) of the desired 7-benzyloxy-2-methyl-1H-quinazolin-4-one as an white solid. ISP mass spectrum, m/e: 267.3 (M+1 calculated for C16H14N2O2: 267).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. customthe precipitate that had formed
  4. filtrationwas filtered off by suction
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-e6a83682e2614ac1abd9f42a5504e1d5
Source dataset
uspto-grants-2007_04
Patent number
US07205309B2

Reaction notes

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