4-tert-Butylbenzoyl chloride → HCID 178440953, compound

HRID 842372Notes

Reaction equation

HRID 842372 reaction equation
[C:1]([C:5]1[CH:41]=[CH:40][C:8]([C:9]([NH:11][C:12]2[CH:39]=[CH:38][CH:37]=[CH:36][C:13]=2[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[CH:23][N:22](S(C4C=CC(C)=CC=4)(=O)=O)[C:21]=3[CH:35]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+](C1C=CC=CC=1C(NC1C=CC2N=CN(S(C3C=CC(C)=CC=3)(=O)=O)C=2C=1)=O)([O-])=O.C(C1C=CC(C(Cl)=O)=CC=1)(C)(C)C.O[Li].O>O1CCOCC1.O>[N:22]1[C:21]2[CH:35]=[C:17]([NH:16][C:14](=[O:15])[C:13]3[CH:36]=[CH:37][CH:38]=[CH:39][C:12]=3[NH:11][C:9](=[O:10])[C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:41][CH:40]=3)[CH:18]=[CH:19][C:20]=2[NH:24][CH:23]=1

Participants

7

Reactant 4

HCID 743724-tert-Butylbenzoyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 18373181HCID 18373181, compoundHCID 18373199HCID 18373199, compound

Product 1

HCID 178440953HCID 178440953, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

By methods substantially equivalent to those described in Examples 1-B and 1-C, 3.7 g (6.5 mmol) of crude 2-[(4-t-butylbenzoyl)amino]-N-(1-tosylbenzimidazol-6-yl)benzamide was prepared from 2-nitro-N-(1-tosylbenzimidazol-6-yl)benzamide and 4-t-butylbenzoyl chloride. This material was dissolved in p-dioxane (50 mL) and a solution of LiOH.H2O (0.48 g, 11 mmol) in water (25 mL) was added with vigorous stirring. After 16 h, the solvents were removed in vacuo and the residue was partitioned between chloroform and satd aq NaHCO3. The phases were separated and the organic phase was washed with water, followed by brine, then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether, filtered and the solid was dissolved in a minimal amount of chloroform and chromatographed over a silica gel column with 10% methanol/chloroform. The product containing fractions were combined and concentrated in vacuo to give 0.97 g (36% overall) of off-white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned between chloroform
  3. customThe phases were separated
  4. washthe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether
  9. filtrationfiltered
  10. dissolutionthe solid was dissolved in a minimal amount of chloroform
  11. customchromatographed over a silica gel column with 10% methanol/chloroform
  12. additionThe product containing fractions
  13. concentrationconcentrated in vacuo
  14. customto give 0.97 g (36% overall) of off-white solid

Sources & evidence

ORD record
ord-b89dcd307bc848e99972d87479c86b57
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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