Tetrapropoxymethane → (6-Chloro-2-propoxy-3-propyl-3H-quinazoline-4-ylidene)propylamine

HRID 1167136Notes

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([NH:9][CH2:10][CH2:11][CH3:12])=NCCC.C(O[C:22]([O:31][CH2:32][CH2:33][CH3:34])(OCCC)OCCC)CC>>[Cl:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[N:1]=[C:22]([O:31][CH2:32][CH2:33][CH3:34])[N:9]([CH2:10][CH2:11][CH3:12])[C:4]2=[CH:4][CH2:3][CH2:2][NH2:1]

Participants

Reactant 2

HCID 548455Tetrapropoxymethane

HCID 112305382-Amino-5-chloro-N,N'-dipropylbenzamidine

Product 1

HCID 53938190(6-Chloro-2-propoxy-3-propyl-3H-quinazoline-4-ylidene)propylamine

Procedure

In a small distillation apparatus 2.5 g (9.8 mmol) of 2-amino-5-chloro-N,N′-dipropylbenzamidine and 3.4 g (13.8 mmol) tetra-n-propylorthocarbonate are heated at 135° C. for 14 hours. Then propanol and excess tetra-n-propylorthocarbonate are distilled off in a water jet vacuum and the residue is purified by column chromatography on silica gel (eluant: hexane/tert.butylmethylether 10:1). Yield: 1.1 g of (6-chloro-2-propoxy-3-propyl-3H-quinazolidine-4-ylidene)propylamine in the form of brownish crystals, m.p. 50-51° C.

Workup

distillationThen propanol and excess tetra-n-propylorthocarbonate are distilled off in a water jet vacuum
customthe residue is purified by column chromatography on silica gel (eluant: hexane/tert.butylmethylether 10:1)

Sources & evidence

ORD record: ord-f6554f3147694f30bd4ef08b417b69e4
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617330B2

Reaction notes

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