Dimethylcarbamoyl Chloride → HCID 22355146, compound

HRID 1110153Notes

Reaction equation

HRID 1110153 reaction equation
[N+:1]1([O-])[C:2]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[N+:14]([O-])=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:8]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.C[N:22]([CH3:26])C(Cl)=O.C[Si]([C:31]#[N:32])(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:31]([C:6]1[N:1]=[C:2]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:26]#[N:22])[N:14]=3)[N:8]=2)[CH:3]=[CH:4][CH:5]=1)#[N:32]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 13528796HCID 13528796, compound

Product 1

HCID 22355146HCID 22355146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2';6',2"-Terpyridine-N,N"-dioxide (7a) (0.96 g, 3.6 mmol) was suspended in dichloromethane (10 ml). N,N-dimethylcarbamyl chloride (0.95 g, 8.8 mmol) and trimethylsilyl cyanide (1.26 g, 12.7 mmol) were added. After stirring for two weeks at room temperature, 10% potassium carbonate was added until the solution was neutral. The phases were separated and the water phase was extracted with chloroform. The chloroform was evaporated and the residue was crystallized from a mixture of acetonitrile and tetrahydrofurane.

Workup

  1. customThe phases were separated
  2. extractionthe water phase was extracted with chloroform
  3. customThe chloroform was evaporated
  4. customthe residue was crystallized from a mixture of acetonitrile and tetrahydrofurane

Sources & evidence

ORD record
ord-d37fcdf6920d445c9a714d4241b8d01b
Source dataset
uspto-grants-1994_06
Patent number
US05324825

Reaction notes

Loading…