Pyrrolidine → 4-Amino-2-methylthio-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline

HRID 727214Notes

Reaction equation

HRID 727214 reaction equation
[C:1]([NH:3][C:4](=[NH:7])[S:5][CH3:6])#[N:2].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.N1CCCC1>>[NH2:2][C:1]1[C:17]2[CH2:16][CH:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[Cl:8])[CH2:20][CH2:19][C:18]=2[N:7]=[C:4]([S:5][CH3:6])[N:3]=1

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 197052584-(2-Chlorophenyl)cyclohexanoneHCID 178504047HCID 178504047, compound

Product 1

HCID 197052704-Amino-2-methylthio-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline

Conditions

Temperature
150 °C

Procedure

A suspension of 1.2 grams of (0.010 mole) of N-cyano-S-methylisothiourea [prepared in the manner disclosed by R. W. Turner; Synthesis, 332 (1975)], 2.1 grams (0.010 mole) of 4-(2-chlorophenyl)cyclohexanone and 0.4 gram (0.005 mole) of pyrrolidine is placed in a glass tube, which is then sealed. The sealed tube is heated at 150° C. for about seven hours. After this time, the sealed tube is cooled in an ice-bath and opened. The reaction mixture is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography using silica gel, yielding 4-amino-2-methylthio-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline.

Workup

  1. customprepared in the manner
  2. customis placed in a glass tube
  3. customwhich is then sealed
  4. temperatureAfter this time, the sealed tube is cooled in an ice-bath
  5. concentrationThe reaction mixture is concentrated under reduced pressure to a residue

Sources & evidence

ORD record
ord-d3e0cb1555ab4e11976f4c19dfb98547
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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