N,N-Dimethylaniline → HCID 60077508, compound

HRID 2110976Notes

Reaction equation

HRID 2110976 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; 1:1.5) 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-92edd400d33843a2963034672bbebc52
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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