Hydrochloric Acid → HCID 20506459, compound

HRID 1577327Notes

Reaction equation

HRID 1577327 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[CH2:18]([O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH3:19].C(N(CC)CC)C.Cl>C(O)CCC.C(O)C>[ClH:12].[CH2:18]([O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][N:27]([C:4]2[N:3]=[C:2]([NH2:1])[C:11]3[C:6](=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([Cl:12])[CH:10]=3)[N:5]=2)[CH2:26][CH2:25]1)[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12920006HCID 12920006, compoundHCID 140223854-(2-Ethoxyethoxy)piperidine

Product 1

HCID 20506459HCID 20506459, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 702EthanolSolvent

Procedure

4-Amino-2,6-dichloro-7,8-dimethoxyquinazoline (4.9 g.), 4-(2-ethoxyethoxy)piperidine (3.2 g.) and triethylamine (10 ml.) in n-butanol (400 ml.) are heated at reflux overnight under an atmosphere of nitrogen. The mixture is then cooled, evaporated in vacuo, and the residue basified (aqueous Na2CO3) and extracted 3 times with chloroform. The combined chloroform extracts are evaporated and the residue chromatographed on neutral alumina to give the crude product which is converted to the hydrochloride salt by treatment with hydrogen chloride in ethanol to afford the title compound.

Workup

  1. temperatureat reflux overnight under an atmosphere of nitrogen
  2. temperatureThe mixture is then cooled
  3. customevaporated in vacuo
  4. extractionextracted 3 times with chloroform
  5. customThe combined chloroform extracts are evaporated
  6. customthe residue chromatographed on neutral alumina
  7. customto give the crude product which

Sources & evidence

ORD record
ord-11f1daed6e734ba9b1de2411bd6c8b37
Source dataset
uspto-grants-1981_09
Patent number
US04287341

Reaction notes

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