Stannous chloride dihydrate → (4-Aminophenyl)-n-[(5-chloro(2-thienyl))sulfonyl]carboxamide

HRID 562670Notes

Reaction equation

HRID 562670 reaction equation
O=C1C2C=CC=CC=2C(=O)[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:20][S:21]([C:24]2[S:25][C:26]([Cl:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[O:19])=[CH:14][CH:13]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[NH2:3][C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:20][S:21]([C:24]2[S:25][C:26]([Cl:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 20800262[4-(1,3-Dioxobenzo[c]azolidin-2-yl)phenyl]-n-[(5-chloro(2-thienyl))sulfonyl]carboxamide

Product 1

HCID 131724995(4-Aminophenyl)-n-[(5-chloro(2-thienyl))sulfonyl]carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 74 mg portion (0.21 mmol) of [4-(1,3-dioxobenzo[c]azolidin-2-yl)phenyl]-N-[(5-chloro(2-thienyl))sulfonyl]-carboxamide, 192 mg (0.84 mmol) of tin dichloride dihydrate were combined and dissolved in 1.4 mL of EtOAc. The mixture was refluxed for 4 h, filtered through celite, and concentrated in vacuo to afford a solid which was purified on silica gel eluting with 10% MeOH/CH2Cl2 to give a quantitative yield of the titled compound. ES-MS (M+H)+=317 (Cl).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo
  4. customto afford a solid which
  5. customwas purified on silica gel eluting with 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d14b3093993c4727b98d0b17ca80b3cb
Source dataset
uspto-grants-2011_11
Patent number
US08067428B2

Reaction notes

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