Water → 4-(4-tert-Butylbenzoylamino)isophthalic acid

HRID 1883079Notes

Reaction equation

HRID 1883079 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].O.[C:15]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>CC(C)=O>[C:15]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[C:11]([OH:13])=[O:12])=[O:24])=[CH:26][CH:27]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 743724-tert-Butylbenzoyl chlorideHCID 113558524-Aminobenzene-1,3-dioic acid

Product 1

HCID 219064144-(4-tert-Butylbenzoylamino)isophthalic acidYield 29%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Into 60 mL acetone was dissolved 0.905 g 5 mmol) 4-aminoisophthalic acid. To the solution was added 30 mL water. The mixture was cooled in an ice bath, and 1.08 mL (5.5 mmol) 4-tert-butylbenzoyl chloride in 10 mL acetone was added dropwise. The mixture was allowed to warm slowlyly to room temperature and after 24 h was concentrated under vacuum and shaken between EtOAc (150 mL) and cold dilute HCl (150 mL). The organic layer was dried (MgSO4) and evaporated. The desired crystalline product (0.489 g, 29%) was obtained from methylene chloride-hexane.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. concentrationwas concentrated under vacuum
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-19035bcdde614772a9b2ae0e57b8c549
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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