1,2-Dichloroethane → HCID 24695862, compound

HRID 446308Notes

Reaction equation

HRID 446308 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=O.[NH2:12][C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:14]=1[CH3:20].C(Cl)CCl>C(Cl)Cl>[NH2:12][C:13]1[CH:18]=[C:17]([NH:19][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=2)[CH:16]=[CH:15][C:14]=1[CH3:20]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 58173,4-Dichlorobenzoic acidHCID 72612,4-Diaminotoluene

Product 1

HCID 24695862HCID 24695862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3,4-dichlorobenzoic acid (200 mg, 1.05 mmol), 2,4-diaminotoluene (513 mg, 4.20 mmol), and EDC (403 mg, 2.10 mmol) was added CH2Cl2 (40 mL). The mixture was stirred overnight at RT, concentrated, diluted with EtOAc and extracted with water. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography (n-Hexanes→50% EtOAc/n-Hexanes) yielding N-(3-amino-4-methyl-phenyl)-3,4-dichloro-benzamide. MS m/z=295, 297 [M]+ and [M+2]+. Calc'd for C14H12Cl2N2O: 295.17.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc
  3. extractionextracted with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (n-Hexanes→50% EtOAc/n-Hexanes)

Sources & evidence

ORD record
ord-156a3cfbcb8c488b91388bc23beb0e63
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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