Carbamic acid, ethyl ester → HCID 135767471, compound

HRID 1762074Notes

Reaction equation

HRID 1762074 reaction equation
[C:1](=[O:6])(OCC)[NH2:2].N[C:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]=1[C:15]#[N:16].[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([NH:22][NH2:23])=O>CN1CCCC1=O>[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]1[N:16]=[C:15]2[N:23]([C:1](=[O:6])[NH:2][C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]=32)[N:22]=1

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 1362882-FluorobenzhydrazideHCID 122517501-Cycloheptene-1-carbonitrile, 2-amino-

Product 1

HCID 135767471HCID 135767471, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of the ethyl carbamate of 1-amino-2-cyanocyclohept-1-ene (11.6 g), o-fluorobenzhydrazide (8.74 g) and 1-methyl-2-pyrrolidone (140 mL) is stirred at reflux under nitrogen for 18 hours, cooled and triturated with water to produce solid material. It is recrystallized from (±)1-methoxy-2-propanol to afford pure 2-(2-fluorophenyl)-8,9,10,11-tetrahydro-7H-cyclohepta[e][1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)one, m.p. 257°-259°, in 63% yield.

Workup

  1. temperatureat reflux under nitrogen for 18 hours
  2. temperaturecooled
  3. customtriturated with water
  4. customto produce solid material
  5. customIt is recrystallized from (±)1-methoxy-2-propanol

Sources & evidence

ORD record
ord-0b875d60641743d988f54bf068d4a095
Source dataset
uspto-grants-1989_05
Patent number
US04831013

Reaction notes

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