Acetic Anhydride → HCID 20392066, compound

HRID 1863141Notes

Reaction equation

HRID 1863141 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(COC)OC>[C:18]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18384010HCID 18384010, compound

Product 1

HCID 20392066HCID 20392066, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 12.5 g. (53 mmoles) of 4-(2-amino-4-tert-butylphenyl)morpholine and 8.7 g. (85 mmoles) of acetic anhydride in 40 ml. of dimethoxyethane was heated at 70° C. for 15 hours. The cooled reaction mixture was then poured into an excess of ice-water and the water mixture extracted twice with 70 ml. of methylene chloride. The combined extracts were dried over anhydrous sodium slfate, filtered and evaporated under reduced pressure. The residue was recrystallized from a 10:1 mixture of n-hexane and chloroform to give 12.5 g. (85%) of the desired product, m.p. 112°-113° C.

Workup

  1. additionA mixture of 12.5 g
  2. customThe cooled reaction mixture
  3. extractionthe water mixture extracted twice with 70 ml
  4. dry with materialThe combined extracts were dried over anhydrous sodium slfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from a 10:1 mixture of n-hexane and chloroform
  8. customto give 12.5 g

Sources & evidence

ORD record
ord-e062ba57e88d413e85db89699a25850b
Source dataset
uspto-grants-1979_09
Patent number
US04168151

Reaction notes

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