Dimethylformamide → HCID 89619537, compound

HRID 2274740Notes

Reaction equation

HRID 2274740 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].S(Cl)([Cl:18])=O.CN(C=O)C>C(Cl)Cl>[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([Cl:18])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 155279394-Hydroxy-3-methoxy-5-nitrobenzoic acid

Product 1

HCID 89619537HCID 89619537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of compound of Example 1a (1.0 eq) in DCM (approx 3.4 vol) is treated with thionyl chloride (1.0-1.2 eq, for example 1.1 eq) and catalytic amount (0.011 eq) of DMF and the mixture is stirred for 16 h at 40° C. DCM is distilled off (approx 2.7 vol) and the residue is diluted with THF (approx 1.8 vol). The excess of thionylchloride is distilled off with THF/DCM and the residue after distillation is cooled to 10° C.

Workup

  1. distillationDCM is distilled off (approx 2.7 vol)
  2. additionthe residue is diluted with THF (approx 1.8 vol)
  3. distillationThe excess of thionylchloride is distilled off with THF/DCM
  4. distillationthe residue after distillation
  5. temperatureis cooled to 10° C.

Sources & evidence

ORD record
ord-e965651e96d24725bfd69053be7f9cf5
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

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