4-Methylphenyl isocyanate → HCID 19807335, compound

HRID 1681211Notes

Reaction equation

HRID 1681211 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:13][S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[CH:9]=2)(=[O:11])=[O:12])=[O:23])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 15841151HCID 15841151, compound

Product 1

HCID 19807335HCID 19807335, compoundYield 33.8%

Procedure

The 5-benzofuransulfonamide (5.74 mmol) and 4-methylphenylisocyanate (5.74 mmol) were reacted as described in Method B above to obtain a solid. This residue was purified by reverse phase chromatography with 50% acetonitrile in water with 1% acetic acid on a C18 column to obtain 0.64 g of the title product as a solid. 1H NMR (CD3SOCD3): κ10.35 (bs, 1 H), 8.74 (s, 1 H), 8.38 (d, J =3 Hz, 1 H), 8.20 (d, J =3 Hz, 1 H), 7.96 (dd, J =3, 9 Hz, 1 H), 7.86 (d, J =9 Hz, 1 H), 7.22 (d, J =9 Hz, 2 H), 7.20 (d, J =3 Hz, 1 H), 7.06 (d, J =9 Hz, 2 H), 2.22 (s, 3 H).

Workup

  1. customto obtain a solid
  2. customThis residue was purified by reverse phase chromatography with 50% acetonitrile in water with 1% acetic acid on a C18 column

Sources & evidence

ORD record
ord-dfcd630bc99844e28a112b7e108d2a14
Source dataset
uspto-grants-1992_12
Patent number
US05169860

Reaction notes

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