N,N-Dimethylaniline → HCID 60077508, compound

HRID 751570Notes

Reaction equation

HRID 751570 reaction equation
C(Cl)(=O)C=O.[F:6][C:7]1[C:8]([O:18][CH3:19])=[C:9](/[CH:14]=[CH:15]\[CH2:16][OH:17])[C:10]([F:13])=[CH:11][CH:12]=1.C[N:21](C)[C:22]1[CH:27]=CC=CC=1.CC[N:31](CC)CC.[OH2:36]>C(Cl)Cl>[N+:21](=[CH:22][C:27]([O:17][CH2:16]/[CH:15]=[CH:14]\[C:9]1[C:10]([F:13])=[CH:11][CH:12]=[C:7]([F:6])[C:8]=1[O:18][CH3:19])=[O:36])=[N-:31]

Participants

7

Reactant 5

HCID 949N,N-DimethylanilineHCID 962WaterHCID 8471TriethylamineHCID 12550982HCID 12550982, compoundHCID 60077543HCID 60077543, compound

Product 1

HCID 60077508HCID 60077508, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The p-toluenesulfonylhydrozone of glyoxylic acid chloride (5.16 g; 0.02 mol) was added to a solution of (2Z)-3-(3,6-difluoro-2-methoxyphenyl)-2-propen-1-ol (3.6 g; 0.018 mol) in dry CH2Cl2 (50 ml) at −5 C, and N,N-dimethylaniline (2.5 ml; 0.02 mol) was added slowly. After stirring for 30 min at −5 C, Et3N (12 ml; 0.09 mol) was added slowly. The resulting mixture was stirred for 15 min at −5 C and then for 30 min at room temperature, whereupon water (˜50 ml) was added. The organic phase was separated washed with water, brine and concentrated in vacuo. Flash chromatography (silica, EA:Hex; 1:15) gave 3.86 g (80%) of product as a yellow solid.

Workup

  1. additionwas added slowly
  2. additionwas added slowly
  3. waitfor 30 min at room temperature
  4. customThe organic phase was separated
  5. washwashed with water, brine
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0e460c755da4c1fa098b3866f8ebe94
Source dataset
uspto-grants-2008_07
Patent number
US07405310B2

Reaction notes

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