Acetic Anhydride → HCID 18993030, compound

HRID 846577Notes

Reaction equation

HRID 846577 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[CH2:10](OC(OCC)OCC)C.C(OC(=O)C)(=O)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH2:36])=[CH:30][CH:29]=1.C([O-])(=O)C.[Na+]>O.C(O)(=O)C>[CH3:9][C:5]1[C:6]2[C:7]([NH:36][CH2:35][CH2:34][C:31]3[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=3)=[N:8][CH:10]=[N:1][C:2]=2[O:3][CH:4]=1

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 674302-(4-Chlorophenyl)ethylamineHCID 517045Sodium AcetateHCID 110188532-AMINO-4-METHYL-3-FURONITRILE

Product 1

HCID 18993030HCID 18993030, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4.0 g of 2-amino-3-cyano-4-methylfuran, 3 cc of triethylorthoformate, and 0.05 cc of acetic anhydride was heated to 135° C. for three hours. Then 5 g of 2-(4-chlorophenyl)ethylamine, 5 cc of glacial acetic acid, and 3.2 g of sodium acetate were added to the reaction mixture. The temperature of the mixture was maintained at 135° C. for three additional hours, after which the mixture was cooled, treated with water and extracted with dichloromethane. The organic phase was then concentrated and washed with water. The solids were extracted from the organic phase with large volumes of ether, which were combined and concentrated to provide 1.07 g of product. M.P. 140° C.

Workup

  1. temperatureThe temperature of the mixture was maintained at 135° C. for three additional hours
  2. temperatureafter which the mixture was cooled
  3. extractionextracted with dichloromethane
  4. concentrationThe organic phase was then concentrated
  5. washwashed with water
  6. extractionThe solids were extracted from the organic phase with large volumes of ether, which
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e7b7a158390417695b48c7e665f1270
Source dataset
uspto-grants-1992_08
Patent number
US05137879

Reaction notes

Loading…