Thiophosgene → HCID 178514691, compound

HRID 1990870Notes

Reaction equation

HRID 1990870 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[OH:8].[C:13](Cl)(Cl)=[S:14]>C1COCC1>[SH:14][C:13]1[O:8][C:7]2[CH:6]=[CH:5][C:4]([S:9]([NH2:12])(=[O:10])=[O:11])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 668142-Aminophenol-4-sulfonamide

Product 1

HCID 178514691HCID 178514691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-4-hydroxy-benzenesulfonamide (5.00 g, 26.6 mmol, 1.0 equiv) in anhydrous THF (250 mL) was added slowly thiophosgene (3.67 g, 2.43 mL, 31.9 mmol, 1.2 equiv) via syringe pump over a time period of 1 h. After stirring for 4 h at rt, excess thiophosgene was quenched by addition of a conc. solution of ammonium chloride (100 mL) and the majority of solvent removed by evaporation under reduced pressure. The residue was extracted with ethyl acetate (3×100 mL) and the combined organic phases dried over MgSO4 yielding 6.1 g (92%) of crude product, which was used in the subsequent reaction step without further purification. 1H NMR (300 MHz, DMSO): δ 7.51 (br s, 2H), 7.68 (s, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.78 (d, J=7.7 Hz, 1H), 14.21 (br s, 1H). 13C NMR (75 MHz, DMSO): δ 106.29, 108.47, 120.06, 129.91, 139.54, 148.16, 179.38. MS (ISP): 230.9 [M+H]+.

Workup

  1. customexcess thiophosgene was quenched by addition of a conc. solution of ammonium chloride (100 mL)
  2. customthe majority of solvent removed by evaporation under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (3×100 mL)
  4. dry with materialthe combined organic phases dried over MgSO4 yielding 6.1 g (92%) of crude product, which
  5. customwas used in the subsequent reaction step without further purification

Sources & evidence

ORD record
ord-e4e2bbb1759e449b8b9bf4eacace3b34
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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