Diethyl Ether → HCID 23438741, compound

HRID 2120175Notes

Reaction equation

HRID 2120175 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C([Mg]Br)C=C.C(OCC)C.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:34][C:33](=[O:35])[C:32]3[CH:36]=[N:37][CH:38]=[CH:39][C:31]=3[N:30]=2)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([NH:30][C:31]2[CH:39]=[CH:38][N:37]=[CH:36][C:32]=2[C:33]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)=[O:35])=[O:34])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 661742-Amino-5-chloropyridineHCID 23438719HCID 23438719, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 23438741HCID 23438741, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-amino-5-chloropyridine (0.11 g, 0.85 mmol) in THF (12 mL) at 0° C. was added a 1 M solution of allylmagnesium bromide in diethyl ether (0.83 mL, 0.83 mmol). After 20 min, 2-[4-t-butylphenyl]-4H-6-aza-3,1-benzoxazin-4-one (0.115 g, 0.41 mmol) was added and the cold bath was removed. After 2 h, the mixture was diluted with ethyl acetate and washed three times with brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The solid was recrystallized from diethyl ether then washed several times with mixtures of ether/hexanes and dried to give 0.138 g (82%) of pale yellow needles.

Workup

  1. customthe cold bath was removed
  2. waitAfter 2 h
  3. additionthe mixture was diluted with ethyl acetate
  4. washwashed three times with brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe solid was recrystallized from diethyl ether
  9. washthen washed several times with mixtures of ether/hexanes
  10. customdried

Sources & evidence

ORD record
ord-fe94389d983f4b0794790b00f1b2c16d
Source dataset
uspto-grants-2004_02
Patent number
US06689780B1

Reaction notes

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