Sodium Hydroxide → Tiodazosin

HRID 971893Notes

Reaction equation

HRID 971893 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:16]([NH2:17])=[N:15][C:14]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4[O:30][C:29]([S:31][CH3:32])=[N:28][N:27]=4)=[O:25])[CH2:20][CH2:19]3)=[N:13][C:8]2=[CH:9][C:10]=1[O:11][CH3:12].Cl>C(O)C>[NH2:17][C:16]1[C:7]2[C:8](=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)[N:13]=[C:14]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([C:26]3[O:30][C:29]([S:31][CH3:32])=[N:28][N:27]=3)=[O:25])[CH2:22][CH2:23]2)[N:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1594277762412-39-9

Product 1

HCID 60891Tiodazosin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Rapid addition of 10 ml. of 1 N sodium hydroxide to a suspension of BL-5111 hydrochloride (5.0 g.) in 50 ml. of rapidly stirred 95% ethanol provides a solution from which the free base begins to precipitate shortly after completing the addition (about 1 min.). The mixture is stirred for a period of 20 min. and the crystalline precipitate collected, washed with water, dried for a period of 24 hr. at 56° C. under high vacuum to afford 4-amino-6,7-dimethoxy-2-[4-(5-methylthio-1,3,4-oxadiazole-2-carbonyl)-piperazin-1-yl]quinazoline (BL-5111) free base, m.p. 228°-230° C.

Workup

  1. additionRapid addition of 10 ml
  2. customto precipitate shortly
  3. additionthe addition (about 1 min.)
  4. customthe crystalline precipitate collected
  5. washwashed with water
  6. customdried for a period of 24 hr

Sources & evidence

ORD record
ord-15b052cb4c0847b3908920000c95ba34
Source dataset
uspto-grants-1979_07
Patent number
US04161595

Reaction notes

Loading…