4-Chloro-6,7-dimethoxyquinazoline → HCID 20263805, compound

HRID 464041Notes

Reaction equation

HRID 464041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[Cl:15].[CH2:16]([NH:20][C:21](=[O:24])[NH:22][NH2:23])[CH2:17][CH2:18][CH3:19]>CCCCCO>[ClH:15].[CH2:4]([NH:23][NH:22][C:21]([NH:20][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1)=[O:24])[CH2:3][CH2:12][CH3:11].[CH2:16]([N:20]([C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1)[C:21](=[O:24])[NH:22][NH2:23])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 12676228N-Butylhydrazinecarboxamide

Product 2

HCID 20263805HCID 20263805, compoundHCID 70068045HCID 70068045, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

3 g of 6,7-dimethoxy-4-chloro-quinazoline were stirred with 3.5 g of 4-n-butyl-semicarbazide in 100 ml of n-amyl alcohol for 2 hours at 100° C. Then, the precipitate which had formed was suction-filtered off, suspended while in hot ethanol and brought to pH 5 by the addition of 2N hydrochloric acid. The clear solution was filtered through charcoal, cooled, suction-filtered and dried in a circulating air drier. The hydrochloride of 4-n-butyl-4-(6,7-dimethoxyquinazol-4-yl)-semi-carbazide, which was obtained with a 70% yield, melted at 216°-217° C. The following compounds were obtained analogously.

Workup

  1. customThen, the precipitate which had formed
  2. filtrationwas suction-filtered off
  3. additionbrought to pH 5 by the addition of 2N hydrochloric acid
  4. filtrationThe clear solution was filtered through charcoal
  5. temperaturecooled
  6. filtrationsuction-filtered
  7. customdried in a circulating air drier

Sources & evidence

ORD record
ord-c31210b9febb4032a445c76e0a168707
Source dataset
uspto-grants-1985_10
Patent number
US04546102

Reaction notes

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