Benzoyl chloride → HCID 15101099, compound

HRID 704577Notes

Reaction equation

HRID 704577 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:22][CH2:21][C:16]3[N:17]=[C:18]([NH2:20])[S:19][C:15]=3[CH2:14]2)[CH2:9][CH2:8]1.C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:22][CH2:21][C:16]3[N:17]=[C:18]([NH:20][C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[S:19][C:15]=3[CH2:14]2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9904970HCID 9904970, compound

Product 1

HCID 15101099HCID 15101099, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (±)-4,5,6,7-tetrahydro-6-[4-(2-pyridinyl)-1-piperazinyl]-2-benzothiazolamine (10.0 g) (Example 1) in 200 ml of chloroform is treated with triethylamine (6.06 g) and benzoyl chloride (4.21 g). The resulting red solution is refluxed for two hours under nitrogen. Saturated sodium bicarbonate solution is added. The organic layer is dried (magnesium sulfate) and evaporated. The residue is purified by MPLC (silica; 1.5% methanol, 98.5% dichloromethane). The title compound is obtained as a yellow solid; mp 230°-232° C.

Workup

  1. temperatureThe resulting red solution is refluxed for two hours under nitrogen
  2. dry with materialThe organic layer is dried (magnesium sulfate)
  3. customevaporated
  4. customThe residue is purified by MPLC (silica; 1.5% methanol, 98.5% dichloromethane)

Sources & evidence

ORD record
ord-0e3adf5c84d0433faad1b0ddf802b46f
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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