Water → 2-Amino-5-[1-(4-ethoxy-quinazolin-6-yl)-meth-(z)-ylidene]-thiazol-4-one

HRID 1783628Notes

Reaction equation

HRID 1783628 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[N:7]=[CH:6][N:5]=1)[CH3:2].COC1C=CC(/C=[C:31]2/[C:32]([NH:34][C:35]([S:37]/2)=[NH:36])=[O:33])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[NH2:36][C:35]1[S:37]/[C:31](=[CH:14]\[C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]=[CH:6][N:5]=[C:4]3[O:3][CH2:1][CH3:2])/[C:32](=[O:33])[N:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 575906244-Ethoxy-quinazoline-6-carbaldehydeHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 116451142-Amino-5-[1-(4-ethoxy-quinazolin-6-yl)-meth-(z)-ylidene]-thiazol-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The suspension of 4-ethoxy-quinazoline-6-carbaldehyde (example 10b) (1 equiv.), pseudothiohydantoin (1 equiv.), and sodium acetate (4 equiv.) in acetic acid was stirred under reflux for 12 h. After cooling to room temperature, water was added. The solid was collected by filtration, washed with water and dried to 2-amino-5-[1-(4-ethoxy-quinazolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 301 (MH+) as a slight yellow solid. LC-MS m/e 256 (MH+).

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. dry with materialdried to 2-amino-5-[1-(4-ethoxy-quinazolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one

Sources & evidence

ORD record
ord-8533b7a9ee9c407d98002ffd5212a1ef
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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