Anisole → HCID 12703443, compound

HRID 1855729Notes

Reaction equation

HRID 1855729 reaction equation
C1(OC)C=CC=CC=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[NH:26][C:25]3=[CH:27][S:28][CH:29]=[C:24]3[NH:23][C:22](=O)[C:21]=2[CH:31]=1.[OH-].[NH4+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(C)C.C1(C)C=CC=CC=1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[NH:26][C:25]3=[CH:27][S:28][CH:29]=[C:24]3[N:23]=[C:22]([N:13]3[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]3)[C:21]=2[CH:31]=1

Participants

8

Reactant 4

HCID 7519AnisoleHCID 14923Ammonium HydroxideHCID 531671-Methylpiperazine2×HCID 12680130HCID 12680130, compound

Product 1

HCID 12703443HCID 12703443, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×HCID 3776IsopropanolSolvent

Procedure

To a solution of 7 ml. of anisole, 3.8 ml. of titanium tetrachloride and 1.5 g. of methylpiperazine in 67 ml. of toluene is added a mixture of 6.7 g. of 7-chloro-4H-thieno-[3,4-b][1,4]benzodiazepin-9(10H)-one and 7.6 g. of methylpiperazine in 7 ml. of toluene. The mixture is refluxed with stirring overnight, cooled and 10 ml. of isopropyl alcohol, 5 g. of diatomaceous earth and 10 ml. of ammonium hydroxide are added. The mixture is filtered and washed with toluene. The toluene is washed with water and then extracted with three 150 ml. portions of 3 N hydrochloric acid. The acid extracts are made alkaline with ammonium hydroxide and extracted with dichloromethane. This extract is dried over magnesium sulfate, filtered and the solvent is evaporated. The residue is crystallized from dichloromethane-hexane giving the desired product, m.p. 191°-194° C.

Workup

  1. additiona mixture of 6.7 g
  2. temperatureThe mixture is refluxed
  3. temperaturecooled
  4. filtrationThe mixture is filtered
  5. washwashed with toluene
  6. washThe toluene is washed with water
  7. extractionextracted with three 150 ml
  8. extractionextracted with dichloromethane
  9. dry with materialThis extract is dried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent is evaporated
  12. customThe residue is crystallized from dichloromethane-hexane giving the desired product, m.p. 191°-194° C.

Sources & evidence

ORD record
ord-3d120cc9aa314ab0ac759c0d43c8fd16
Source dataset
uspto-grants-1980_08
Patent number
US04216148

Reaction notes

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