1,1'-Thiocarbonyldiimidazole → HCID 14611141, compound

HRID 569829Notes

Reaction equation

HRID 569829 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:29](N2C=NC=C2)=[S:30])C=1>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:9](=[O:10])[C:11]2[C:12](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:29]1=[S:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 12380728HCID 12380728, compound

Product 1

HCID 14611141HCID 14611141, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-[2-(N-benzylcarbamoyl)-anilino]acetate (1.5 g) and N,N'-thiocarbonyldiimidazole (2.85 g) was stirred at 120° C. for 30 minutes. After cooling, the reaction mixture was diluted with chloroform and chromatographed on silica gel. Elution with chloroform gave ethyl 2-(3-benzyl-1,2,3,4-tetrahydro-4-oxo-2-thioxoquinazolin-1-yl)acetate. A mixture of ethyl 2-(3-benzyl-1,2,3,4-tetrahydro-4-oxo-2-thioxoquinazolin-1-yl)acetate and 1N sodium hydroxide (2 ml) in methanol (10 ml) was stirred for 4 hours at room temperature. The reaction mixture was poured into dilute hydrochloric acid and extracted with chloroform. The extract was washed with brine and dried. Removal of the solvent gave 2-(3-benzyl-1,2,3,4-tetrahydro-4-oxo-2-thioxoquinazolin-1-yl)acetic acid (280 mg).

Workup

  1. temperatureAfter cooling
  2. customchromatographed on silica gel
  3. washElution with chloroform

Sources & evidence

ORD record
ord-1faf1f80992a42119b2a98e09d7ce68e
Source dataset
uspto-grants-1988_03
Patent number
US04734419

Reaction notes

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