Ammonium Chloride → HCID 178440037, compound

HRID 267208Notes

Reaction equation

HRID 267208 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2=[C:8]([CH3:14])[N:9]=[C:10]([CH2:11][CH2:12][CH3:13])[N:4]2[N:3]=1.[CH2:15]([Mg]Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>CCOCC>[NH2:1][C:2]1[NH:7][CH:6]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2=[C:8]([CH3:14])[N:9]=[C:10]([CH2:11][CH2:12][CH3:13])[N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12493505HCID 12493505, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 178440037HCID 178440037, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Amino-5-methyl-7-propylimidazo[5,1-f]-as-triazine (Example 4) (1.9 g.) was added to benzyl magnesium chloride (prepared from benzyl chloride (6.3 g.) and magnesium (1.2 g.)) in ether (400 ml.), and the mixture was stirred for 4 hours at room temperature. Aqueous ammonium chloride (50 ml., 20%) was added and the aqueous layer was separated and extracted with ethyl acetate. The extracts were dried over magnesium sulphate, filtered and evaporated and the residue was chromatographed on silica gel (100 g.). Fractions eluted with ethyl acetate were discarded. The fractions eluted with a mixture of ethyl acetate and methanol (4:1) were evaporated to give 2-amino-4-benzyl-3,4-dihydro-5-methyl-7-propylimidazo [5,1-f]-as-triazine as a gum (0.83 g.). This gum (0.7 g.) and acetyl chloride (0.3 ml.) in glacial acetic acid (10 ml.) were heated at 100° for 2.5 hours. Acetic acid was distilled off and the residue was crystallised from a mixture of ethanol and ethyl acetate to give a white solid, m.p. 240°-241°.

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was chromatographed on silica gel (100 g.)
  7. washFractions eluted with ethyl acetate
  8. washThe fractions eluted with a mixture of ethyl acetate and methanol (4:1)
  9. customwere evaporated

Sources & evidence

ORD record
ord-80e0d4449289416bb202be71a9d4393c
Source dataset
uspto-grants-1976_03
Patent number
US03941785

Reaction notes

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