Water → HCID 973597, compound

HRID 2290661Notes

Reaction equation

HRID 2290661 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[OH-].[Na+].Cl[C:15]([O:17][CH3:18])=[O:16].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:15]([O:17][CH3:18])=[O:16])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 227703,4-Dimethoxyaniline

Product 1

HCID 973597HCID 973597, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 15.3 g (0.1 mol) of 3,4-dimethoxyaniline in 60 mL of methylene chloride was treated with 55 mL of 2N sodium hydroxide. The reaction mixture was cooled to -5° C. and 7.4 mL (0.096 mol) of methyl chloroformate was added keeping the reaction temperature between 15°-25° C. The reaction was stirred 1.5 hr at 10°-20° C. and then 50 mL of water was added. The layers were separated and the aqueous layer was extracted with 4×100 mL of methylene chloride. The combined methylene chloride layers were dried over sodium sulfate and Darco treated. Evaporation gave a paste which was recrystallized from 10 mL of ethyl acetate and 10 mL of hexanes to give 18.4 g (98%) of the product, mp 83°-87° C. NMR (CDCl3) δ 3.75 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 6.63 (br s, 1H, NH), 6.73 (m, 2H, ArH), 7.13 (m, 1H, ArH).

Workup

  1. custombetween 15°-25° C
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 4×100 mL of methylene chloride
  4. dry with materialThe combined methylene chloride layers were dried over sodium sulfate and Darco
  5. additiontreated
  6. customEvaporation
  7. customgave a paste which
  8. customwas recrystallized from 10 mL of ethyl acetate and 10 mL of hexanes

Sources & evidence

ORD record
ord-e36f34de0b7045ad953b803953501041
Source dataset
uspto-grants-1986_10
Patent number
US04617417

Reaction notes

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