Dichloromethane → HCID 2806365, compound

HRID 1599528Notes

Reaction equation

HRID 1599528 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.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([S:28]([NH:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 2806365HCID 2806365, compoundYield 906.3%

Procedure

To 4.6 g (3.03 mmol) of the methyl 3-aminobenzoate prepared in Example 1 in 30 mL of methylene chloride containing 4.0 mL (36 mmol) of N-methylmorpholine was added 4.0 mL (33 mmol) of benzenesulfonyl chloride. After stirring at room temperature for 1 hr the reaction mixture was quenched with water (100 mL). The suspension was dissolved in ethyl acetate/ether combination. The organic phase was washed sequentially with 2N HCl and then sodium bicarbonate. The organic phase was dried (MgSO4), and concentrated and triturated from ethyl acetate/hexane ether to give 8.0 g (90%) of the title compound as a colorless solid: NMR (DMSO-d6 ; 300 MHz) δ 10.58 (s, 1H), 7.75-7.84 (m, 3H), 7.52-7.72 (m, 4H), 7.35-7.45 (m, 2H), and 3.82 ppm (s, 3H).

Workup

  1. customwas quenched with water (100 mL)
  2. dissolutionThe suspension was dissolved in ethyl acetate/ether combination
  3. washThe organic phase was washed sequentially with 2N HCl
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customtriturated from ethyl acetate/hexane ether

Sources & evidence

ORD record
ord-caa8d9f9cdf94d1983e95d78c90d7488
Source dataset
uspto-grants-1998_04
Patent number
US05741819

Reaction notes

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