Dimethylformamide → HCID 22397197, compound

HRID 411236Notes

Reaction equation

HRID 411236 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:11](=[O:21])(=[O:20])[C:12]3[CH:19]=[CH:18][S:17][C:13]=3[N:14]([CH3:16])[N:15]=2)=[O:9])=[CH:4][CH:3]=1.CN(C=O)C.[Br:29]N1C(=O)CCC1=O>C(Cl)Cl>[Br:29][C:18]1[S:17][C:13]2[N:14]([CH3:16])[N:15]=[C:10]([C:8]([NH:7][CH2:6][C:5]3[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[S:11](=[O:21])(=[O:20])[C:12]=2[CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 22397217HCID 22397217, compound

Product 1

HCID 22397197HCID 22397197, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing N-(4-chlorobenzyl)-1-methyl-1H-thieno[2,3-e][1,3,4]-thiadiazine-3-carboxamide 4,4-dioxide (Preparation 56, 0.14 g) and anhydrous DMF (2 mL) is stirred under nitrogen while adding N-bromosuccinimide (0.074 g) in one portion. This solution is stirred overnight at room temperature before diluting with CH2Cl2 (50 mL) and washing with water (60 mL). The organic portion is separated and washed with brine, dried over Na2SO4, filtered, and concentrated to give a brown oil. Physical characteristics: MS (ESI+) m/z 448 (M+H)+, 450.

Workup

  1. stirringThis solution is stirred overnight at room temperature
  2. washwashing with water (60 mL)
  3. customThe organic portion is separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil

Sources & evidence

ORD record
ord-61b37039b4fe439e8223b6af002e80c4
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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