Dimethylamine → HCID 57837618, compound

HRID 888111Notes

Reaction equation

HRID 888111 reaction equation
F[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(C1NC=CN=1)(C1NC=CN=1)=[S:13].C([O-])([O-])=O.[K+].[K+].CNC.[CH3:33][N:34]([CH:36]=O)[CH3:35]>COCCOC>[CH3:35][N:34]([CH3:33])[C:36]1[S:13][C:2]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=2[N:4]=1

Participants

7

Reactant 5

HCID 674Dimethylamine2×HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 677852-Fluoro-5-nitroanilineHCID 11412697Thiocarbonyl diimidazole

Product 1

HCID 57837618HCID 57837618, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-Fluoro-5-nitroaniline (1.7 g), thiocarbonyl diimidazole (1.9 g) and K2CO3 (2.9 g) were suspended in dry DME (20 mL) and stirred at RT for 12 h. 20 mL of DMF and dimethyl amine (40% in water, 8 mL) were added and the resulting mixture was heated at 65° C. for 3 h and 12 h at RT. Reaction was followed by LCMS and more dimethyl amine was added (5 mL) and heated again until reaction was almost completed. Solvent was evaporated and residue was dissolved in water. Mixture was extracted with EtOAc and filtered on silica pad. Solvent was removed to give N,N-dimethyl-5-nitrobenzo[d]thiazol-2-amine.

Workup

  1. temperaturethe resulting mixture was heated at 65° C. for 3 h and 12 h at RT
  2. customReaction
  3. additionwas added (5 mL)
  4. temperatureheated again until reaction
  5. customSolvent was evaporated
  6. dissolutionresidue was dissolved in water
  7. extractionMixture was extracted with EtOAc
  8. filtrationfiltered on silica pad
  9. customSolvent was removed

Sources & evidence

ORD record
ord-d5dbd62f3e874a78b9052bec1d7611ed
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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