Dimethylformamide → HCID 86600692, compound

HRID 1191501Notes

Reaction equation

HRID 1191501 reaction equation
O1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=O)C1.[C:12]([O-:15])([O-])=O.[Cs+].[Cs+].[Cl:18][CH2:19][CH2:20][CH2:21]I.C[N:24](C=O)C>>[Cl-:18].[CH:20]1([CH2:12][O:15][N:24]=[C:7]2[CH2:6][CH:5]3[NH2+:4][CH:3]([CH2:9][CH2:10]3)[CH2:8]2)[CH2:21][CH2:19]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 813631-Chloro-3-iodopropane

Product 1

HCID 86600692HCID 86600692, compound

Procedure

A reaction flask or vial was charged 4H-benzo[1,4]oxazin-3-one (1.0 equiv) dissolved in DMF (0.1 g/ml), Cs2CO3 (1.5 equiv) and 1-chloro-3-iodopropane (1.1 equiv). The reaction was stirred in rt for 60-70 h and evaporated to dryness. The reaction was redissolved in H2O and extracted with EtOAc 3×150 ml. The combined organic phases were dried over Na2SO4 and concentrated to a crude that was used directly or purified by column chromatography (heptanes/EtOAc).

Workup

  1. customevaporated to dryness
  2. dissolutionThe reaction was redissolved in H2O
  3. extractionextracted with EtOAc 3×150 ml
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to a crude that
  6. custompurified by column chromatography (heptanes/EtOAc)

Sources & evidence

ORD record
ord-e1fad3e57a0e4a70a03c102430ffa70a
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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