Thionyl Chloride → 4-acetylamino-5-chloro-2-methoxy-N-[1-(2-thenyl)-4-piperazinyl]-benzamide

HRID 2286509Notes

Reaction equation

HRID 2286509 reaction equation
[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[NH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[S:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1>[OH-].[Na+]>[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([NH:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[S:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)=[O:11])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 23461656N-amino-N'-2-thenylpiperazine

Product 1

HCID 234616524-acetylamino-5-chloro-2-methoxy-N-[1-(2-thenyl)-4-piperazinyl]-benzamideYield 64%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-Acetylamino-5-chloro-2-methoxybenzoic acid (3.67 g, 0.015 mole) was treated with thionyl chloride (30 ml) at 50° for 1/2 hour. The mixture was evaporated in vacuo and the residue azeotroped twice with anhydrous toluene (100 ml), redissolved in hot anhydrous toluene (150 ml) and filtered. Triethylamine (2 ml) was added to the filtrate followed by N-amino-N'-2-thenylpiperazine (2.70 g, 0.0137 mole) and the reaction left for 6 hours at room temperature. The mixture was basified with 10% sodium hydroxide (10 ml) and the toluene layer separated, dried over K2CO3 and evaporated in vacuo to yield 4-acetylamino-5-chloro-2-methoxy-N-[1-(2-thenyl)-4-piperazinyl]-benzamide (3.7 g, 64%) as colourless microcrystals, m.p. 178°-181° C. (ex EtOAc-light petroleum 40°-60°).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue azeotroped twice with anhydrous toluene (100 ml)
  3. dissolutionredissolved in hot anhydrous toluene (150 ml)
  4. filtrationfiltered
  5. additionTriethylamine (2 ml) was added to the filtrate
  6. customthe toluene layer separated
  7. dry with materialdried over K2CO3
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a9914522679742b89b9ff76098f192f6
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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