Dichloromethane → HCID 19010701, compound

HRID 1741760Notes

Reaction equation

HRID 1741760 reaction equation
C(Cl)Cl.[C:4](Cl)(=[O:8])[C:5]([CH3:7])=[CH2:6].[CH2:10]([N:17]([CH2:24][CH2:25][OH:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(N(CC)CC)C>[CH2:10]([N:17]([CH2:24][CH2:25][O:26][C:4](=[O:8])[C:5]([CH3:7])=[CH2:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 13528Methacryloyl chlorideHCID 10680815HCID 10680815, compound

Product 1

HCID 19010701HCID 19010701, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1000 ml of dried methylene chloride are placed in a 4 l sulfonating vessel at 0° C. together with 334 g of methacrylic acid chloride. A mixture of 500 ml of dried methylene chloride, 323 of dried triethylamine and 454 of N-benzyl-N(β-hydroxyethyl)aniline, (the compound of formula 1a) are added drop by drop to this mixture at 0°-10° C. The reaction mixture is allowed to rise to room temperature slowly and is controlled on a thin layer chromatograph (silica gel) solvent: toluene/acetic acid ester 2:1. After the end of the reaction (after standing overnight), the reaction mixture is filtered and washed three times with one liter of a 10% aqueous NaOH solution and finally four times each time with 1 l of water. The organic phase is then dried over sodium sulphate and the solvent is removed in a rotary evaporator. 482 g of the product of formula 1d ##STR15## results.

Workup

  1. customat 0° C.
  2. customto rise to room temperature
  3. customAfter the end of the reaction (after standing overnight)
  4. filtrationthe reaction mixture is filtered
  5. washwashed three times with one liter of a 10% aqueous NaOH solution and finally four times each time with 1 l of water
  6. dry with materialThe organic phase is then dried over sodium sulphate
  7. customthe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-96337e7de061488c94b6a1916c296798
Source dataset
uspto-grants-1994_08
Patent number
US05334710

Reaction notes

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