Dimethylformamide → HCID 22397197, compound

HRID 1070654Notes

Reaction equation

HRID 1070654 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-440803a9780f4cb3bb28923bd41fc3c6
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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