Hydrochloric Acid → HCID 28068545, compound

HRID 2265164Notes

Reaction equation

HRID 2265164 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[S:14]([C:17]1[C:25]2[C:21](=[N:22][S:23][N:24]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].N1C=CC=CC=1.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=1[NH:1][S:14]([C:17]1[C:25]2=[N:24][S:23][N:22]=[C:21]2[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 80001Methyl 4-chloroanthranilateHCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-

Product 1

HCID 28068545HCID 28068545, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-amino-4-chlorobenzoate (7.0 g, 37.7 mmol) in DCM (75 mL) at room temperature (rt) was added 4-chlorosulfonyl-2,1,3-benzothiadiazole (9.45 g, 39.6 mmol), pyridine (9.1 mL, 112 mmol), and DMAP (0.23 g, 1.88 mmol). The mixture was stirred at rt overnight, poured into 1 N HCl (200 mL), and extracted with DCM (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (hexanes/EtOAc) to afford the title sulfonamide as a tan solid (11.65 g, 80%). MS (ESI−): mass calcd. for C14H10ClN3O4S2, 383.8; m/z found, 382 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.38 (s, 1H), 8.40 (dd, J=7.2, 1.2, 1H), 8.24 (dd, J=8.8, 1.2, 1H), 7.80 (d, J=8.4, 1H), 7.76 (d, J=2.0, 1H), 7.74 (dd, J=8.8, 7.2, 1H), 6.94 (dd, J=8.4, 2.0, 1H), 3.92 (s, 3H). Anal. calcd. for C14H10ClN3O4S2: C, 43.81; H, 2.63; N, 10.95. Found: C, 44.19; H, 3.00; N, 11.23.

Workup

  1. extractionextracted with DCM (2×100 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-d2498d02c05a49efb492c29bf8d6c816
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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