Ethyl orthopropionate → HCID 86733629, compound

HRID 1659101Notes

Reaction equation

HRID 1659101 reaction equation
C(O[C:4]([O:10][CH2:11][CH3:12])(OCC)[CH2:5][CH3:6])C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[CH2:23][S:22][C:21]2=[S:26])=[CH:16][CH:15]=1>C(OC(=O)C)(=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[C:24](=[O:25])[C:23](=[C:4]([O:10][CH2:11][CH3:12])[CH2:5][CH3:6])[S:22][C:21]2=[S:26])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 66995Ethyl orthopropionateHCID 83070Rhodanine, 3-(4-chlorophenyl)-

Product 1

HCID 86733629HCID 86733629, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Following the procedures of Example 1, triethylorthopropionate is reacted with 3-(4'-chlorophenyl)-rhodanine in acetic anhydride for 51/2 hours to give 3-(4'-chlorophenyl)-5-(1'-ethoxypropylidene)-rhodanine. To a suspension of the latter (25 g., 0.0765 m.) in 200 ml. of dioxane and 200 ml. of water is added 50 ml. of 10% sodium hydroxide solution. The mixture is stirred at room temperature for 4 hours and then concentrated in vacuo at 40°-45°C. The residual solution is washed with ether, decolorized and acidified with dilute hydrochloric acid to yield 3-(4'-chlorophenyl)-5-(1'-hydroxypropylidene)-rhodanine, m.p. 145°-149°C.

Sources & evidence

ORD record
ord-0440b6fd77b24722b8f9249d8fb479d3
Source dataset
uspto-grants-1976_06
Patent number
US03966942

Reaction notes

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