Chloro-N,N-dimethylformiminium chloride → HCID 15463651, compound

HRID 1106455Notes

Reaction equation

HRID 1106455 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[C:8](=[O:11])[C:7]1[C:12]([OH:20])=[C:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[CH:15][C:6]=1[O:5]2.[Cl-].Cl[CH:23]=[N+:24]([CH3:26])[CH3:25].C([BH3-])#N.[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:23][N:24]([CH3:26])[CH3:25])[C:8](=[O:11])[C:7]1[C:12]([OH:20])=[C:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[CH:15][C:6]=1[O:5]2

Participants

6

Reactant 3

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 5003444Sodium cyanoborohydrideHCID 9796118HCID 9796118, compound

Product 1

HCID 15463651HCID 15463651, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 60 mg (0.20 mmol) of 2-chloro-6,8-dihydroxy-7-propyl-9H-pyrrolo [2,1-b][1,3]benzoxazin-9-one in 20 mL of CH2Cl2 was added 157 mg (1.22 mmol) of chloromethylene dimethylammonium chloride and the reaction stirred for 1 hr. The mixture was concentrated, diluted with 50 mL of dry MeOH and 1.0 g (15.9 mmol) of sodium cyanoborohydride was added. After 24 hr the mixture was quenched with saturated NaHCO3 and the mixture extracted with ethylacetate which was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (Silica Gel EtOAc 100% to acetone 100%) to give 50 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwas added
  3. customAfter 24 hr the mixture was quenched with saturated NaHCO3
  4. extractionthe mixture extracted with ethylacetate which
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (Silica Gel EtOAc 100% to acetone 100%)

Sources & evidence

ORD record
ord-8e8b96411cb84db0bd3fa293c46f4439
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Reaction notes

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