Hydrochloric Acid → HCID 20452668, compound

HRID 1462379Notes

Reaction equation

HRID 1462379 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13]C(C)(C)[NH:11][C:10](=[O:16])[C:9]=2[CH:17]=1.[ClH:18]>C(N)C1C=CC=CC=1>[ClH:18].[CH2:10]([NH:11][CH2:2][CH2:3][O:4][C:5]1[CH:17]=[C:9]([C:10]([NH2:11])=[O:16])[C:8]([OH:13])=[CH:7][CH:6]=1)[C:9]1[CH:17]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 137544136-(2-Bromoethoxy)-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one

Product 1

HCID 20452668HCID 20452668, compound

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

A suspension of 60 g of 6-(2-bromoethoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one in 110 ml of benzylamine is heated, with stirring, for 30 minutes in a bath at 80°. The reaction mixture is thereupon adjusted with conc. hydrochloric acid, using ice-cooling, to a pH value of about 3, and is allowed to stand until crystallisation occurs. The crystals are filtered off with suction after 4 hours, washed with 100 ml each of water and of ethyl acetate, and dried. The crude 5-(2-benzylamino-ethoxy)-salicylamide hydrochloride obtained melts at 214°-216°. The base liberated therefrom melts at 107°-108° (from ethyl acetate/ether).

Workup

  1. temperatureis heated
  2. temperaturecooling, to a pH value of about 3
  3. customto stand until crystallisation
  4. filtrationThe crystals are filtered off with suction after 4 hours
  5. washwashed with 100 ml each of water and of ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-2d4c633055e648cfb97436f1688d1961
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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