Cesium carbonate → HCID 10185868, compound

HRID 430952Notes

Reaction equation

HRID 430952 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:24]=[CH:23][C:14]3[N:15]([CH3:22])[C:16](=[O:21])[NH:17][S:18](=[O:20])(=[O:19])[C:13]=3[CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+:33]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Br)=[CH:38][CH:37]=1)([O-:35])=[O:34]>CN(C)C=O.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:24]=[CH:23][C:14]3[N:15]([CH3:22])[C:16](=[O:21])[N:17]([CH2:40][C:39]4[CH:42]=[CH:43][C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=4)[S:18](=[O:19])(=[O:20])[C:13]=3[CH:12]=2)=[O:10])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 69808061HCID 69808061, compound

Product 1

HCID 10185868HCID 10185868, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

4-Methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide (1.0 g), and cesium carbonate (0.87 g) were mixed in 50 mL of N,N-dimethylformamide. 4-Nitrobenzylbromide (0.58 g) was added, and the resulting mixture was stirred for 16 hours at room temperature. The reaction was diluted with IM HCl and filtered to give a gummy solid. Recrystallization from ethyl alcohol gave the title compound as a white solid (0.77 g). 1H-NMR (CDCl3); δ 8.48 (s, 1H), 8.26 (d, 1H), 8.10 (m, 3H), 7.54 (d, 2H), 7.25 (m, 4H), 6.82 (t, 2H), 5.05 (s, 2H), 4.50 (d, 2H), 3.73 (d, 3H), and 3.48 (s, 3H) ppm. Anal. (C24H22N407S-1.01H2O) C,H,N. MS: M++1=511.2 Da

Workup

  1. filtrationfiltered
  2. customto give a gummy solid
  3. customRecrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-c436ded0f82943878b46c4d24580aa83
Source dataset
uspto-grants-2003_12
Patent number
US06656932B2

Reaction notes

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