Ethylene Glycol → HCID 56617002, compound

HRID 280549Notes

Reaction equation

HRID 280549 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][N:22]=2)[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[O:7])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[O:29]1CC[CH2:31][CH2:30]1.C(O)CO>C(N(CC)CC)C>[CH2:30]1[O:29][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:10]2[CH:20]=[CH:21][N:22]=[C:8]([C:6](=[O:7])[C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:9]=2)[O:12][CH2:31]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 13562483HCID 13562483, compound

Product 1

HCID 56617002HCID 56617002, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-(4-Chlorobenzoyl)-isonicotinanilide (11 g) was reacted with thionyl chloride as in Synthesis 1. To the resulting product, tetrahydrofuran (150 ml) and ethylene glycol (30 ml) were added and the mixture was stirred for about 20 minutes under cooling with ice. To the resulting solution, triethylamine (25 ml) was added dropwise. After completion of the addition, the solution was stirred for 1 hour, followed by stirring at room temperature for another 4 hours. The resulting solution was treated as in Synthesis 1 to produce the titled compound in an amount of 10.2 g (yield: 80%). m.p. 102°-103° C.

Workup

  1. temperatureunder cooling with ice
  2. additionAfter completion of the addition
  3. stirringthe solution was stirred for 1 hour
  4. stirringby stirring at room temperature for another 4 hours
  5. additionThe resulting solution was treated as in Synthesis 1

Sources & evidence

ORD record
ord-6f25f3d345584061b72dfdfb6f981cf4
Source dataset
uspto-grants-1986_05
Patent number
US04590198

Reaction notes

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