Dimethylformamide → HCID 19006189, compound

HRID 1742925Notes

Reaction equation

HRID 1742925 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.CN(C=O)C.O=S(Cl)Cl.[CH2:20]([CH:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:27]O)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:27][CH:26]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acidHCID 953372-Hexyl-1-decanol

Product 1

HCID 19006189HCID 19006189, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 6-chloronicotinic acid (47.4 g, 0.3 mol) in xylene (150 ml) containing DMF (1.5 ml) was stirred and heated at 80° C. whilst SOCl2 (26.1 ml, 0.36 mol) was added during 20 minutes. Stirring and heating at 80° C. was continued for 11/2 hours, when all had passed into solution. Excess SOCl2, HCl, and a little xylene were then removed by distillation at 20 mm pressure. The residual solution was cooled to 40° C., and 2-hexyldecanol (72.9 g, 0.3 mol) was added during 20 minutes, the temperature rising to 55° C.

Workup

  1. additionwas added during 20 minutes
  2. stirringStirring
  3. custom2 hours, when
  4. customExcess SOCl2, HCl, and a little xylene were then removed by distillation at 20 mm pressure
  5. temperatureThe residual solution was cooled to 40° C.
  6. customrising to 55° C.

Sources & evidence

ORD record
ord-a632ae7d9a404239ae7beb882218d508
Source dataset
uspto-grants-1994_08
Patent number
US05342937

Reaction notes

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