Water → 2-[1-[(Aminocarbonyl)oxy]ethyl]-6-methylpyrazolo[1,5-c]quinazolin-5(6H)-one

HRID 65686

Reaction equation

HRID 65686 reaction equation
[OH:1][CH:2]([C:4]1[CH:16]=[C:15]2[N:6]([C:7](=[O:18])[N:8]([CH3:17])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[N:5]=1)[CH3:3].[O-:19][C:20]#[N:21].[Na+].FC(F)(F)C(O)=O.O>C1C=CC=CC=1>[NH2:21][C:20]([O:1][CH:2]([C:4]1[CH:16]=[C:15]2[N:6]([C:7](=[O:18])[N:8]([CH3:17])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)[N:5]=1)[CH3:3])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 129616082-(1-hydroxyethyl)-6-methylpyrazolo[1,5-c]quinazolin-5(6H)-one

Product 1

HCID 129616072-[1-[(Aminocarbonyl)oxy]ethyl]-6-methylpyrazolo[1,5-c]quinazolin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 3.7 g (0.0172 mole) of 2-(1-hydroxyethyl)-6-methylpyrazolo[1,5-c]quinazolin-5(6H)-one in 30 ml of benzene there is added 2.6 g (0.036 mole) of solid, 90% sodium cyanate followed by the dropwise addition of 3.1 ml (0.041 mole) of trifluoroacetic acid. The reaction mixture is stirred on a magnetic stirrer at approximately 120 revolutions per minute for 2 hours at room temperature. By the end of this time a gum separates. The reaction mixture is subsequently treated with 15 ml of water with increased stirring speed after which a solid (insoluble in either phase) forms. This is filtered, washed with water and air dried to give 2.9 g (60% direct yield), m.p. 216°-221°. The solid is twice crystallized from chloroform-methanol (1:1) to give 2.0 g of analytically pure material, m.p. 250°-252°.

Workup

  1. temperaturewith increased
  2. stirringstirring speed after which a solid (insoluble in either phase) forms
  3. filtrationThis is filtered
  4. washwashed with water and air
  5. customdried
  6. customto give
  7. custom2.9 g (60% direct yield), m.p. 216°-221°
  8. customThe solid is twice crystallized from chloroform-methanol (1:1)
  9. customto give 2.0 g of analytically pure material, m.p. 250°-252°

Sources & evidence

ORD record
ord-d6300e909cbf4732a7250d8e25bac2a8
Source dataset
uspto-grants-1978_12
Patent number
US04128644

Linked notes

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