Dimethylformamide → HCID 89619537, compound

HRID 2274741Notes

Reaction equation

HRID 2274741 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
10 °C

Procedure

A suspension of compound of Example 1a (1.0 eq) in DCM (approx 4.5 vol) is treated with thionyl chloride (1.0-1.2 eq, for example 1.1 eq) and catalytic amount (0.0055 eq) of DMF and the mixture is stirred for 16 h at reflux. Unreacted thionylchloride is distilled off with DCM and the residue after distillation is diluted with THF (approx 1.8 vol) and cooled to 10° C.

Workup

  1. temperatureat reflux
  2. distillationUnreacted thionylchloride is distilled off with DCM
  3. distillationthe residue after distillation
  4. additionis diluted with THF (approx 1.8 vol)

Sources & evidence

ORD record
ord-50b76e83efe44ccdaeb9585f0dba7c72
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

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