Pyridine → HCID 59243147, compound

HRID 1644608Notes

Reaction equation

HRID 1644608 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:19])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:19][S:31]([C:27]2[S:26][CH:30]=[CH:29][CH:28]=2)(=[O:33])=[O:32])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 855182-Thiophenesulfonyl chlorideHCID 11288356Methyl 2-amino-5-(benzyloxy)benzoate

Product 1

HCID 59243147HCID 59243147, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 5-(benzyloxy)-2-(amino)benzoate ([116027-17-9], 1.3 g, 5.06 mmol) was stirred in DCM (20 mL) and pyridine (1.2 mL) at 0° C. Thiophene-2-sulfonyl chloride (1.02 g, 5.56 mmol) was added. After one hour, the cooling bath was removed and the reaction was stirred overnight. The mixture was washed once with 10% aqueous HCl. The organics were dried and concentrated. Chromatography (20 to 40% ethyl acetate in hexanes) gave the title compound. [M+H] calc'd for C19H17NO5S2, 404; found, 404.

Workup

  1. customat 0° C
  2. customthe cooling bath was removed
  3. washThe mixture was washed once with 10% aqueous HCl
  4. customThe organics were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd0afefad7a14965a3c1258f6beb05d2
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

Loading…