Methanol → HCID 68912341, compound

HRID 1191437Notes

Reaction equation

HRID 1191437 reaction equation
I[CH2:2][CH:3]([CH3:17])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12](C)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16].CC[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].[CH3:25][OH:26]>>[CH3:25][O:26][C:12]1[CH:13]=[CH:14][C:9]2[O:8][CH2:7][C:6](=[O:16])[N:5]([CH2:4][C@H:3]([CH3:17])[CH2:2][N:20]3[CH2:21][CH2:22][CH:7]([O:8][CH2:9][CH2:10][CH3:11])[CH2:24][CH2:23]3)[C:10]=2[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 689085494-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68912341HCID 68912341, compound

Conditions

Temperature
60 °C

Procedure

A 7 mL vial was charged with the crude 4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one (1 equiv), Et3N (0.5 mL) and the secondary amine (1.2-1.5 equiv). This mixture was shaken at 60° C. for 72 h and thereafter diluted with MeOH (10 mL) and concentrated with basic Al2O3 (2 g) and purified by flash chromatography.

Workup

  1. concentrationconcentrated with basic Al2O3 (2 g)
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1d2ba32926034811b4547a25fcb3ea9e
Source dataset
uspto-grants-2014_03
Patent number
US08680115B2

Reaction notes

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