Phosgene → HCID 13092019, compound

HRID 434827Notes

Reaction equation

HRID 434827 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:22][CH2:23][CH3:24])=[C:13]([CH:15]([OH:21])[C:16](=[NH:20])[O:17]CC)[CH:14]=1.[O:25]1CCC[CH2:26]1.C(Cl)(Cl)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:22][CH2:23][CH3:24])=[C:13]([CH:15]2[O:21][C:26](=[O:25])[NH:17][C:16]2=[O:20])[CH:14]=1

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13599066HCID 13599066, compound

Product 1

HCID 13092019HCID 13092019, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

By the procedure of Example 54, but using only 2.3 equivalents of triethylamine, ethyl 1-(5-chloro-2-ethoxyphenyl)-1-hydroxymethanecarboximidate (8.0 g., 0.029 mole) in 300 ml. of tetrahydrofuran was reacted with phosgene. After stirring for 2 hours at room temperature, isolation was also according to Example 54, substituting chloroform for ethyl acetate, resulting in toluene recrystallized 5-(5-chloro-2-ethoxyphenyl)oxazolidine-2,4-dione (2.7 g., m.p. 197°-199° C.).

Workup

  1. customrecrystallized 5-(5-chloro-2-ethoxyphenyl)oxazolidine-2,4-dione (2.7 g., m.p. 197°-199° C.)

Sources & evidence

ORD record
ord-9f5b0fec79ef4112a8b203a9fd0c277f
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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