Hydrochloric Acid → HCID 89619537, compound

HRID 2274742Notes

Reaction equation

HRID 2274742 reaction equation
[Cl:1]CCl.[OH:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17].S(Cl)(Cl)=O.Cl>CN(C)C=O>[OH:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:8]([C:9]([Cl:1])=[O:10])=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 155279394-Hydroxy-3-methoxy-5-nitrobenzoic acid

Product 1

HCID 89619537HCID 89619537, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In a reactor 68 kg dichloromethane, 20 kg 5-nitro-vanillic acid of example 1b, 76 gram of N,N-dimethylformamide and 13.4 kg (8 L) thionyl chloride, was charged at 20.2° C. The mixture was heated to 40° C. until all the starting material dissolved and the evolution of HCl and SO2 stopped. When all the starting material was consumed 5-10 L dichloromethane was distilled off at normal pressure at 40° C. then the mixture was cooled to 20-25° C. and the distillation was continued until dry under vacuum at 40° C. The evaporation residue was dissolved in 36 kg dry THF. The THF solution was used in Example 4d.

Workup

  1. dissolutiondissolved
  2. customWhen all the starting material was consumed 5-10 L dichloromethane
  3. distillationwas distilled off at normal pressure at 40° C.
  4. temperaturethe mixture was cooled to 20-25° C.
  5. distillationthe distillation
  6. customuntil dry under vacuum at 40° C
  7. dissolutionThe evaporation residue was dissolved in 36 kg dry THF

Sources & evidence

ORD record
ord-e5b4d55d7b1244be89fe6e9d8f5c0d1b
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

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