Thionyl Chloride → HCID 20291879, compound

HRID 1413349Notes

Reaction equation

HRID 1413349 reaction equation
[N:1]([C:4]1[CH:22]=[CH:21][CH:20]=[C:6]2[C:7]([N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[C:10](=[O:11])[C:5]=12)=[O:8])=[N+:2]=[N-:3].S(Cl)([Cl:25])=O>CN(C)C=O>[N:1]([C:4]1[CH:22]=[CH:21][CH:20]=[C:6]2[C:7]([N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([Cl:25])=[O:18])[C:10](=[O:11])[C:5]=12)=[O:8])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20291877HCID 20291877, compound

Product 1

HCID 20291879HCID 20291879, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

15.0 g (0.05 mol) of the 6-(3-azidophthalimidyl)-caproic acid obtained according to Example 8 are dissolved in 327 g (2.75 mols) of thionyl chloride, and the solution is warmed to 80° C., the operations being carried out under yellow light. At 80° C., 0.5 ml of N,N-dimethylformamide is added to the clear solution obtained. The reaction mixture is stirred for 15 minutes at 80° C. and is then cooled to room temperature. This produces a beige-coloured suspension, which is filtered with suction, under N2. The crude product is recrystallised from 250 ml of dry ligroin. 12.5 g (75.4% of theory) of 6-(3-azidophthalimidyl)-caproyl chloride are obtained; melting point 68°-69° C.

Workup

  1. customobtained
  2. temperatureis then cooled to room temperature
  3. customThis produces a beige-coloured suspension, which
  4. filtrationis filtered with suction, under N2
  5. customThe crude product is recrystallised from 250 ml of dry ligroin

Sources & evidence

ORD record
ord-3a8bacd80418467284e0f37409c20db3
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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