Ethyl (chloroformyl)acetate → HCID 135966498, compound

HRID 1090092Notes

Reaction equation

HRID 1090092 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([CH2:18][CH3:19])[C:15]([NH2:17])=[S:16])[CH:8]=2)[N:3]=1.[CH:20]([CH:22](Cl)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=O>CN(C)C=O>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([C:15]3[S:16][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][N:17]=3)[CH2:18][CH3:19])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 136116205HCID 136116205, compound

Product 1

HCID 135966498HCID 135966498, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the thiourea (4.67 g), ethyl formylchloroacetate (Archiv der Pharmazie, 1953, 286, 494; 2.55 g) and dimethylformamide (25 ml) was stirred and heated to 100° C. for 1 hour. The mixture was cooled, filtered and the filtrate was evaporated. The residue was partitioned between methylene chloride and a saturated aqueous sodium bicarbonate solution. The organic solution was dried over sodium sulphate, filtered and evaporated. The residue was purified by trituration in ethyl acetate to give ethyl 2-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-ethylamino]thiazole-5-carboxylate (1.37 g), m.p. 188°-192° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customThe residue was partitioned between methylene chloride
  5. dry with materialThe organic solution was dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by trituration in ethyl acetate

Sources & evidence

ORD record
ord-c6bf0deb4f414c7ca870b4c526f99795
Source dataset
uspto-grants-1992_01
Patent number
US05081124

Reaction notes

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