Water → HCID 19386964, compound

HRID 2399328Notes

Reaction equation

HRID 2399328 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C:8]([CH2:13][NH:14][OH:15])=[C:7]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[C:6]=2[CH:23]=1.C[Si]([N:28]=[C:29]=[O:30])(C)C.O.ClCCl>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:11])([CH3:12])[C:8]([CH2:13][N:14]([OH:15])[C:29]([NH2:28])=[O:30])=[C:7]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[C:6]=2[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 70696Trimethylsilyl isocyanateHCID 19387043HCID 19387043, compound

Product 1

HCID 19386964HCID 19386964, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-2,2-dimethyl-3-(hydroxyamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.300 g, 0.0795 mol) in tetrahydrofuran was added dropwise trimethylsilyl isocyanate (0.22 ml, 0.18 g, 0.0016 mol) at room temperature under nitrogen. The reaction mixture was stirred overnight at room temperature. Water and dichloromethane were added. The organic layer was separated, dried and evaporated to give crude product which was chromatographed on silica gel, eluting with dichloromethane/methanol (90/10) to afford 0.24 g (72%) of 6-bromo-2,2-dimethyl-3-(N-hydroxyureido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 216° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated
  4. customto give crude product which
  5. customwas chromatographed on silica gel
  6. washeluting with dichloromethane/methanol (90/10)

Sources & evidence

ORD record
ord-85ced1a156ef4402b2d3644e97c3efcc
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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