Dimethylformamide → HCID 67298168, compound

HRID 1520303Notes

Reaction equation

HRID 1520303 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C[N:18](C=O)C>O=S(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:5]=1[C:6]([NH2:18])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 127191782-Nitro-5-propoxybenzoic acid

Product 1

HCID 67298168HCID 67298168, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-nitro-5-propoxy-benzoic acid (1.97 g, 8.75 mmol) and DMF (0.1 mL) in SOCl2 (20 mL) was stirred at 65° C. for 2 h. After the reaction was completed, the mixture was cooled to room temperature. SOCl2 was removed in vacuo and the residue was dissolved in anhydrous CH2Cl2 (10 mL), which was added to NH3—H2O (28%) dropwise. After 1 h, the precipitate was collected and dried in vacuo to give 1.68 g of i-a as a yellow solid (85.2%). LCMS m/z=208.1 (M−16), 225.1 (M+1) (Method B) (retention time=1.88 min).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. customSOCl2 was removed in vacuo
  3. dissolutionthe residue was dissolved in anhydrous CH2Cl2 (10 mL)
  4. additionwhich was added to NH3—H2O (28%) dropwise
  5. waitAfter 1 h
  6. customthe precipitate was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6fa2de3290c544e681388b79ca95d6df
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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