Ammonia → alpha-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethyl]-aminomethyl]-2-furanmethanol

HRID 1462368Notes

Reaction equation

HRID 1462368 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[O:6][CH:7]=[CH:8][CH:9]=1)[OH:4].CC1(C)[NH:16][C:15](=[O:17])[C:14]2[CH:18]=[C:19]([O:22][CH2:23][CH2:24]Br)[CH:20]=[CH:21][C:13]=2[O:12]1.N>C(O)(C)C>[C:15]([C:14]1[CH:18]=[C:19]([CH:20]=[CH:21][C:13]=1[OH:12])[O:22][CH2:23][CH2:24][NH:1][CH2:2][CH:3]([C:5]1[O:6][CH:7]=[CH:8][CH:9]=1)[OH:4])(=[O:17])[NH2:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 27564412-Furanmethanol, alpha-(aminomethyl)-HCID 137544136-(2-Bromoethoxy)-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

Product 1

HCID 20452660alpha-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethyl]-aminomethyl]-2-furanmethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7.0 g of α-(aminomethyl)-2-furan-methanol and 7.5 g of 2,3-dihydro-2,2-dimethyl-6-(2-bromoethoxy)-4H-1,3-benzoxazin-4-one is melted and the melt is stirred for 1 hour in a bath at about 110°. 50 ml of isopropanol and 2 ml of concentrated ammonia solution are added to the reaction mixture whilst this is still warm, the mixture is boiled for 5 minutes and filtered and the filtrate is allowed to cool. After working up, α-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethyl]-aminomethyl]-2-furanmethanol with a melting point of 169°-171° is obtained.

Workup

  1. temperaturethis is still warm
  2. waitthe mixture is boiled for 5 minutes
  3. filtrationfiltered
  4. temperatureto cool

Sources & evidence

ORD record
ord-954cfce1021c435fb0aee2983bb8a4ac
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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