Water → HCID 3045474, compound

HRID 1732759Notes

Reaction equation

HRID 1732759 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[C:24]([Cl:25])=[CH:23][C:12]2[C:13](=O)[CH2:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[S:17][C:11]=2[CH:10]=1.O>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:8][C:9]1[C:24]([Cl:25])=[CH:23][C:12]2[C:13]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[S:17][C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 12271947HCID 12271947, compound

Product 1

HCID 3045474HCID 3045474, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

1-Methylpiperazine (15.0 g), followed by titanium tetrachloride (3.1 g) in benzene (45 ml), was added to a warm solution of 7,8-dichlorodibenzo(b,f)thiepine-10(11H)-one (8.85 g) (its preparation is described in Example 8) in benzene (75 ml). The mixture was refluxed while stirring for 28 hours, cooled and decomposed with water (100 ml). The resultant precipitate was filtered and washed with benzene and water. The benzene layer in the filtrate was separated, washed with water, dried over magnesium sulfate and taken down. The enamine base, obtained in nearly quantitative yield, was purified by crystallization from ethanol, m.p. 157°-159° C. Neutralization with maleic acid in ethanol yields the maleate, C23H22Cl2N2O4S, which is crystallized from ethanol; m.p. 229°-232° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturecooled
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with benzene and water
  5. customThe benzene layer in the filtrate was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-403ceff99e2c4098969a96b20e714b48
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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