3-Chlorobenzoic Acid → HCID 21831680, compound

HRID 1648693Notes

Reaction equation

HRID 1648693 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[S:12]([C:37]1[CH:60]=[CH:59][C:40]2=[N:41][N:42]([C:44]3[CH:49]=[C:48]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:47]=[C:46]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:45]=3[OH:58])[N:43]=[C:39]2[CH:38]=1)[C:13]1[CH:36]=[CH:35][C:16]2=[N:17][N:18]([C:20]3[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:21]=3[OH:34])[N:19]=[C:15]2[CH:14]=1.[OH-:61].[Na+].ClC1C=C(C=CC=1)C(O)=O>C(Cl)Cl>[S:12]([C:37]1[CH:60]=[CH:59][C:40]2=[N:41][N:42]([C:44]3[CH:49]=[C:48]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:47]=[C:46]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:45]=3[OH:58])[N:43]=[C:39]2[CH:38]=1)([C:13]1[CH:36]=[CH:35][C:16]2=[N:17][N:18]([C:20]3[CH:25]=[C:24]([C:26]([CH3:27])([CH3:28])[CH3:29])[CH:23]=[C:22]([C:30]([CH3:31])([CH3:32])[CH3:33])[C:21]=3[OH:34])[N:19]=[C:15]2[CH:14]=1)(=[O:6])=[O:61]

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21218135HCID 21218135, compound

Product 1

HCID 21831680HCID 21831680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.9 g (0.022 mole) of m-chloroperoxybenzoic acid 55% in 50 mL of methylene chloride is added at 25°-27° C. to a solution of 6.8g (0.01 mole) 5,5'-thio-bis-[2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole], prepared in Example 17, in 150 mL of methylene chloride over a period of 15 minutes. The resulting exotherm is controlled with ice cooling. In short order precipitation of product and m-chlorobenzoic acid takes place. After stirring the reaction for 3 hours, there is added 1.2 g (0.03 mole) of sodium hydroxide as a 4% aqueous solution to dissolve the m-chlorobenzoic acid. Methylene chloride is removed from the reaction mixture under partial vacuum and diluted with 75 mL of methanol. The product is filtered and the filter cake thoroughly washed with water and methanol to give 6.5 g. of the title compound, mp.>300° C.

Workup

  1. customIn short order precipitation of product and m-chlorobenzoic acid
  2. customthe reaction for 3 hours
  3. customMethylene chloride is removed from the reaction mixture under partial vacuum
  4. additiondiluted with 75 mL of methanol
  5. filtrationThe product is filtered
  6. washthe filter cake thoroughly washed with water and methanol
  7. customto give 6.5 g

Sources & evidence

ORD record
ord-c5bba89567fd482a8aef1be22cf4ccb8
Source dataset
uspto-grants-1995_07
Patent number
US05436349

Reaction notes

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