Diethyl acetylenedicarboxylate → HCID 85815316, compound

HRID 2177211Notes

Reaction equation

HRID 2177211 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2OC(=O)[S:10][N:9]=2)=[CH:4][CH:3]=1.[C:14]([O:23][CH2:24][CH3:25])(=[O:22])[C:15]#[C:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>ClC1C=CC=C(Cl)C=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:15]([C:14]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 8194535-(4-chlorophenyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 85815316HCID 85815316, compound

Reagents, catalysts & solvents 1

HCID 109431,3-DichlorobenzeneSolvent

Conditions

Temperature
148 °C

Procedure

Into a 150-mL sealed tube, was placed 5-(4-chlorophenyl)-2H-1,3,4-oxathiazol-2-one (2 g, 9.65 mmol, 1.00 equiv), 1,4-diethyl but-2-ynedioate (3.29 g, 19.33 mmol, 2.00 equiv), 1,3-dichlorobenzene (30 mL). The resulting solution was stirred for 16 h at 148° C. The resulting mixture was concentrated under vacuum. This resulted in 1 g (31%) of 4,5-diethyl 3-(4-chlorophenyl)-1,2-thiazole-4,5-dicarboxylate as brown oil.

Workup

  1. customInto a 150-mL sealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 1 g (31%) of 4,5-diethyl 3-(4-chlorophenyl)-1,2-thiazole-4,5-dicarboxylate as brown oil

Sources & evidence

ORD record
ord-57b46c9f4bc448f982ca58f7962476f4
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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