Carbamic acid, ethyl ester → HCID 136116269, compound

HRID 1413812Notes

Reaction equation

HRID 1413812 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[C:5]([NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1)=O.[C:23](=O)([O:25]CC)[NH2:24].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[C:12]([C:11]1[CH:17]=[C:18]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:5]([C:4]1[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=1[O:2][CH3:1])[NH:24][C:23]2=[O:25])([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 14812Phosphorus oxide (P4O10)HCID 1739885HCID 1739885, compound

Product 1

HCID 136116269HCID 136116269, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl 4-(2'-methoxy-benzoylamino)-benzoate (21 g), prepared according to Example 19 is reacted with ethyl carbamate (12 g) and P2O5 (70 g) in xylene (200 ml) for 6 hours at the reflux temperature. After cooling, the precipitate is filtered off, poured in ice-water and treated with NaOH to neutralization. The precipitate (23 g) is collected by filtering and is hydrolyzed by treatment with LiBr (10 moles/mole) in dimethylformamide (150 ml) at the reflux temperature for 2 hours. After cooling, acidify with acetic acid, filter and wash with hot ethanol to obtain 6-carboxy-2-(2'-methoxy-phenyl)-3,4-dihydro-4-oxo-quinazoline (14.7 g; m.p. 296°-297° C.).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off
  3. additionpoured in ice-water
  4. additiontreated with NaOH to neutralization
  5. customThe precipitate (23 g) is collected
  6. filtrationby filtering
  7. temperatureAfter cooling
  8. filtrationfilter
  9. washwash with hot ethanol

Sources & evidence

ORD record
ord-3bfc67c71477487ab87b6a903e777696
Source dataset
uspto-grants-1981_02
Patent number
US04251531

Reaction notes

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