Ethanol → Terazosin

HRID 1067914Notes

Reaction equation

HRID 1067914 reaction equation
C(O)C.[O:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10].[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[C:20](Cl)[N:19]=1>O>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:18]([NH2:17])=[N:19][C:20]([N:14]3[CH2:13][CH2:12][N:11]([C:9]([CH:5]4[O:4][CH2:8][CH2:7][CH2:6]4)=[O:10])[CH2:16][CH2:15]3)=[N:21][C:22]2=[CH:23][C:24]=1[O:30][CH3:31]

Participants

5

Reactant 3

HCID 702EthanolHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 27346411-(Tetrahydro-2-furoyl)piperazine

Product 1

HCID 5401TerazosinYield 101.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of absolute ethanol (272 ml), water (68 ml) and N-(2-tetrahydrofuroyl)piperazine (20 g) were added, while stirring, 4-amino-2-chloro-6,7-dimethoxyquinazoline (22.2 g). The reaction mixture was heated to reflux and the reflux was maintained for about 32 hours. Then the reaction mixture was cooled to room temperature and stirred at this temperature for about 48 hours. The crystals were collected by filtration, washed with absolute ethanol and dried in vacuo at 40° C. to yield 36.44 g (85.5%) of Terazosin.HCl dihydrate. See Trial M in Table I. Trial N was performed using a 10% volume of water.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturethe reflux was maintained for about 32 hours
  4. stirringstirred at this temperature for about 48 hours
  5. filtrationThe crystals were collected by filtration
  6. washwashed with absolute ethanol
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-6974a168f6cd404a8e52a190cb51185e
Source dataset
uspto-grants-2001_06
Patent number
US06248888B1

Reaction notes

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