Dichloromethane → HCID 735094, compound

HRID 744727Notes

Reaction equation

HRID 744727 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(Cl)Cl.CN1CCOCC1.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32](Cl)(=[O:34])=[O:33]>>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:33])=[O:34]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 71252-Naphthalenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 735094HCID 735094, compoundYield 97.6%

Procedure

To 5.0 g (33 mmol) of methyl 3-aminobenzoate (4) in 70 mL of methylene chloride containing 4.0 mL (36 mmol) of N-methylmorpholine was added 7.49 g (33 mmol) of 2-naphthalenesulfonyl chloride. After stirring at room temperature overnight, the reaction mixture was quenched with 1N HCl (100 mL). The suspension was dissolved in ca. 250 mL of tetrahydrofuran and enough ether was added to induce phase separation. The organic extract was washed with saturated sodium chloride solution (2×). The organic phase was dried (MgSO4), and concentrated to give 11.0g (97% yield) of the title compound as a pale yellow solid: 1H-NMR (200 MHz; DMSO-d6) δ8.46 (s, 1H), 8.13 (t, 2H), 7.99 (d, 1H), 7.55-7.75 (m, 5H), 7.43 (dd, 21H), 7.38 (d, 1H), 3.79 ppm (s, 3H).

Workup

  1. customthe reaction mixture was quenched with 1N HCl (100 mL)
  2. dissolutionThe suspension was dissolved in ca. 250 mL of tetrahydrofuran
  3. additionenough ether was added
  4. customphase separation
  5. extractionThe organic extract
  6. washwas washed with saturated sodium chloride solution (2×)
  7. dry with materialThe organic phase was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fb65f55b4bd3407296e8e901e1f1913b
Source dataset
uspto-grants-1996_09
Patent number
US05559150

Reaction notes

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