Dimethylcarbamoyl Chloride → HCID 54443352, compound

HRID 1292535Notes

Reaction equation

HRID 1292535 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]2[C:13]2[C:17]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=3[O:15][N:14]=2)=[CH:3][CH:2]=1.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>N1C=CC=CC=1>[CH3:23][N:24]([CH3:28])[C:25](=[O:26])[O:22][C:20]1[CH:19]=[CH:18][C:17]2[C:13]([CH:8]3[CH2:9][NH:10][CH2:11][CH2:12][N:7]3[C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[N:14][O:15][C:16]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 135984214HCID 135984214, compound

Product 1

HCID 54443352HCID 54443352, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazol-6-ol (0.80 g) in pyridine (10 ml) was added dimethylcarbamyl chloride (0.70 g) under N2. The reaction was heated to 85° C. for 2 hours. TLC (silica gel 30% MeOH/CH2Cl2) showed no starting material was present. The solvent was removed in vacuo and the residue was flash chromatographed (silica gel) eluting with 7% MeOH/CH2Cl2 to afford 0.80 g of material. The material was further purified through recrystallization from CH2Cl2 /pet. ether to afford 0.70 g of the product, m.p. 171°-172° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customchromatographed (silica gel)
  3. washeluting with 7% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5f8b28d9191d4a16a8d3b658fc458494
Source dataset
uspto-grants-1998_05
Patent number
US05756754

Reaction notes

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