Diisopropylethylamine → 3-[(Phenylsulfonyl)amino]-N-[(4-hydroxy-3-methoxyphenyl)methyl]benzamide

HRID 1599529Notes

Reaction equation

HRID 1599529 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C1=CC=CC=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.Cl.[OH:57][C:58]1[CH:65]=[CH:64][C:61]([CH2:62][NH2:63])=[CH:60][C:59]=1[O:66][CH3:67]>CN(C)C=O>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:63][CH2:62][C:61]2[CH:64]=[CH:65][C:58]([OH:57])=[C:59]([O:66][CH3:67])[CH:60]=2)=[O:16])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)HCID 7922013-Benzenesulfonamidobenzoic acid

Product 1

HCID 189289473-[(Phenylsulfonyl)amino]-N-[(4-hydroxy-3-methoxyphenyl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 139 mg (0.5 mmol) of 3-(phenylsulfonyl)aminobenzoic acid as prepared in Example 9 in 1 mL of N,N-dimethylformamide was added sequentially 1 mL of 0.5M (0.5 mmol) of Castro's reagent (benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) in N,N-dimethylformamide and then 500 μL of N,N-diisopropylethylamine. After 5 min, 95 mg (0.5 mmol) of 4-hydroxy-3-methoxybenzylamine HCl was added. After 30 min, the reaction mixture was quenched with 7 mL of 2N HCl, extracted into ethyl acetate (2×2 mL), washed with water (3×4 mL) and then sat. NaHCO3 (1×4 mL). The organic phase was passed through a Waters solid phase extraction column (5 g silica gel) onto which was added Na2SO4 to act a drying agent. Elution with ethyl acetate gave the title compound: NMR (DMSO-d6 ; 300 MHz) δ 10.46 (s, 1H), 8.88 (t, 1H), 8.84 (s, 1H), 7.74-7.81 (m, 3H), 7.50-7.70 (m, 6H), 7.30 (t, 1H) 7.22 (d, 1H), 6.87 (s, 1H), 6.69 (t, 2H), 4.31 (d, 2H), 3.73 ppm (s, 3H). Mass spectrum (MALDI-TOF; gentisic acid matrix) cald. for C27H20N2O5S: 435.1 (M+Na). Found: 435.0.

Workup

  1. waitAfter 30 min
  2. customthe reaction mixture was quenched with 7 mL of 2N HCl
  3. extractionextracted into ethyl acetate (2×2 mL)
  4. washwashed with water (3×4 mL)
  5. extractionThe organic phase was passed through a Waters solid phase extraction column (5 g silica gel) onto which
  6. additionwas added Na2SO4
  7. washElution with ethyl acetate

Sources & evidence

ORD record
ord-2004a225f6e34d958b4c3cb209c7b13d
Source dataset
uspto-grants-1998_04
Patent number
US05741819

Reaction notes

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