Cesium carbonate → HCID 22291126, compound

HRID 967892Notes

Reaction equation

HRID 967892 reaction equation
Br[CH2:2][CH:3]1[O:5][CH2:4]1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:16]=2)=[CH:9][C:8]=1[NH:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(N(C)C)=O>O>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[CH:16]=2)=[CH:9][C:8]=1[NH:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:2][CH:3]2[O:5][CH2:4]2)[CH:31]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 18430EpibromohydrinHCID 31374DimethylacetamideHCID 22291011HCID 22291011, compound

Product 1

HCID 22291126HCID 22291126, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Bromo-2,3-epoxypropane (1.5 ml) was added to a stirred mixture of N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-hydroxybenzamide (1.5 g), caesium carbonate (2.84 g) and DMA (100 ml) and the resultant solution was stirred at ambient temperature for 18 hours. The mixture was poured into water (750 ml). The precipitate was isolated, washed with water and dried under vacuum at 60° C. There was thus obtained the title compound (1.3 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.73 (m, 1H), 2.85 (m, 1H), 3.2 (t, 4H), 3.75 (t, 4H), 3.91 (m, 1H), 4.43 (m, 1H), 7.2 (m, 3H), 7.37 (m, 4H), 7.66 (m, 3H), 7.56 (m, 3H), 7.8 (s, 1H), 9.9 (s, 1H), 10.14 (s, 1H); Mass Spectrum: M−H− 486.

Workup

  1. customThe precipitate was isolated
  2. washwashed with water
  3. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-adcc158325fe4c25a265d6df88ea4f0f
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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