Dichloromethane → HCID 22397175, compound

HRID 411222Notes

Reaction equation

HRID 411222 reaction equation
BrN1C(=O)CCC1=O.[CH3:9][N:10]1[C:15]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=2[S:13](=[O:22])(=[O:21])[C:12]([C:23]([O:25][CH3:26])=[O:24])=[N:11]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(Cl)Cl>ClC(Cl)C.CN(C=O)C>[CH3:9][N:10]1[C:15]2[CH:16]=[CH:17][C:18]([CH2:20][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:19][C:14]=2[S:13](=[O:22])(=[O:21])[C:12]([C:23]([O:25][CH3:26])=[O:24])=[N:11]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 67184N-bromobutanimideHCID 22397147HCID 22397147, compound

Product 1

HCID 22397175HCID 22397175, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

N-Bromosuccinimide (0.239 g) and methyl 1,6-dimethyl-1H-4,1,2-benzothiadiazine-3-carboxylate 4,4-dioxide (Preparation 40, 0.30 g) are dissolved in dichloroethane (100 mL). The solution is exposed to light from a 650 W sunlamp with stirring for 25 minutes. The solvent is evaporated and the crude solid obtained is dissolved in DMF (8 mL). Morpholine (0.43 g) is added and the mixture is stirred for 3 hours. The mixture is poured into CH2Cl2 (200 mL) and washed with water (3×200mL). The organic layer is dried with Na2SO4, filtered and the solvent evaporated. The crude solid is chromatographed with MeOH/CH2Cl2 (1-5%) to obtain 0.23 g (59%) of the title compound as an off-white solid. Physical characteristics: MS (ESI+) m/z 254 (M+H).

Workup

  1. customThe solvent is evaporated
  2. customthe crude solid obtained
  3. stirringthe mixture is stirred for 3 hours
  4. washwashed with water (3×200mL)
  5. dry with materialThe organic layer is dried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude solid is chromatographed with MeOH/CH2Cl2 (1-5%)

Sources & evidence

ORD record
ord-b66b46c3fccf40bc961f3a6a3e2248f9
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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