Thionyl Chloride → HCID 15231841, compound

HRID 1707398Notes

Reaction equation

HRID 1707398 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17]O)[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:21][CH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[CH:13]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54298000HCID 54298000, compound

Product 1

HCID 15231841HCID 15231841, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide was added dropwise to 4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-propanol (1.06 g) until a solution was obtained. Thionyl chloride (0.63 mL) was added and the reaction mixture was heated for 45 minutes before being evaporated to dryness. The residue was taken up in ice water then made basic with saturated sodium bicarbonate solution. The resulting precipitate was collected and dried to provide 0.32 g of a dark brown solid. This material was purified by silica gel column chromatography eluting with 85:15 methylene chloride:methanol to provide 0.28 g of the desired product as a solid m.p. 245°-247° C. Analysis: Calculated for C13ClH17N4 +1.5H2 0: % C, 53.51; % H, 6.91; % N, 19.2; Found: % C, 53.81; % H, 6.25; % N, 18.86.

Workup

  1. customwas obtained
  2. temperaturethe reaction mixture was heated for 45 minutes
  3. custombefore being evaporated to dryness
  4. customThe resulting precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-eb3e6dec24e14073af59c888ef73a326
Source dataset
uspto-grants-1994_10
Patent number
US05352784

Reaction notes

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