Ethyl (chloroformyl)acetate → HCID 135966498, compound

HRID 981770Notes

Reaction equation

HRID 981770 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-d2009f15efbc47e0a34af7c41c1c355f
Source dataset
uspto-grants-1991_02
Patent number
US04992550

Reaction notes

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