Thionyl Chloride → HCID 23461665, compound

HRID 2286501Notes

Reaction equation

HRID 2286501 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[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1>>[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[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:24][CH2:23]2)=[O:11])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 121984534-Benzylpiperazin-1-amine

Product 1

HCID 23461665HCID 23461665, compoundYield 58%

Procedure

4-Acetylamino-5-chloro-methoxybenzoic acid (3.50 g, 0.144 mole) was treated with thionyl chloride (25 ml) at 50° for 1/2 hour. The mixture was evaporated in vacuo and the residue azeotroped twice with anhydrous benzene (100 ml) and redissolved in anhydrous benzene (100 ml). Triethylamine (1.45 g) was added followed by 1-amino-4-benzylpiperazine (2.75 g 0.144 mole) and the reaction left for 6 hours at room temperature. The mixture was evaporated in vacuo, taken up in water (50 ml) basified with dilute sodium hydroxide (10%) and extracted with chloroform. Evaporation of the dried (MgSO4) chloroform extract gave 4-acetylamino-5-chloro-2-methoxy-N-[4-benzyl-1-piperazinyl]benzamide (3.50 g; 58%) as colourless microcrystals m.p. 211°-213° C. A sample recrystallised from benzene gave m.p. 212° C.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue azeotroped twice with anhydrous benzene (100 ml)
  3. dissolutionredissolved in anhydrous benzene (100 ml)
  4. additionTriethylamine (1.45 g) was added
  5. customThe mixture was evaporated in vacuo
  6. extractionextracted with chloroform
  7. customEvaporation of the
  8. dry with materialdried (MgSO4) chloroform
  9. extractionextract

Sources & evidence

ORD record
ord-d37c80c395ba4579aa44cfd354d85b67
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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