HCID 12771163, compound → HCID 12912477, compound

HRID 1680834Notes

Reaction equation

HRID 1680834 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]([CH3:18])=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26](C1C=CC=CC=1Cl)[CH:27]=N>C(OCC)(=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[C:4](=[O:6])[C:3]2[C:2](=[C:11]([CH3:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH3:18])[CH:8]=2)[N:1]=[CH:27]1

Participants

4

Reactant 2

HCID 12771163HCID 12771163, compoundHCID 23454775HCID 23454775, compound

Product 1

HCID 12912477HCID 12912477, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture consisting of 500 mg of methyl 2-amino-4-ethoxycarbonyl-3,5-dimethylbenzoate and 640 mg of N,N-bis-(o-chlorophenyl)-formamidine was heated to 200° C. with occasional swirling in an open flask. The temperature of the mixture was maintained at around 200° C. for 1.5 hours. After cooling, the mixture was taken up in ethyl acetate, and then, the organic extract was washed with dilute hydrochloric acid, and with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated. The resulting residue was chromatographed on silica gel to give 385 mg (54% of theory) of 3-(2-chlorophenyl)-7-ethoxycarbonyl-6,8-dimethyl-4(3H)-quinazolinone melting at 151°-152° C. (recryst. from ethanol). 1H NMR: δ(CDCl3) 1.49 (t, 3H), 2.46 (s, 3H), 2.62 (s, 3H), 4.48 (q, 2H), 7.30-7.70 (m, 4H), 7.93 (s, 1H), 8.06 (s, 1H).

Workup

  1. customwith occasional swirling in an open flask
  2. temperatureThe temperature of the mixture was maintained at around 200° C. for 1.5 hours
  3. temperatureAfter cooling
  4. extractionthe organic extract
  5. washwas washed with dilute hydrochloric acid
  6. dry with materialwith water, and dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customThe resulting residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c6375975d559466ebc9923ac61e6e385
Source dataset
uspto-grants-1981_06
Patent number
US04276295

Reaction notes

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