Tetrahydrofuran → HCID 13093541, compound

HRID 544320Notes

Reaction equation

HRID 544320 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[O:25][CH3:26])[C:10](=[NH:14])[O:11]CC.[O:27]1CCC[CH2:28]1>>[CH3:26][O:25][C:16]1[CH:17]=[CH:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]=1[CH:9]1[O:8][C:28](=[O:27])[NH:11][C:10]1=[O:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 20459941HCID 20459941, compound

Product 1

HCID 13093541HCID 13093541, compound

Procedure

By the procedure of Example 12, except that 2.3 rather than 2.0 equivalents of triethylamine were used, ethyl 1-hydroxy-1-(2-methoxy-1-naphthyl)methanecarboximidate (16.5 g., 0.063 mole) in 500 ml. of tetrahydrofuran was converted to crude product. Recrystallization from ethyl acetate/toluene gave purified 5-(2-methoxy-1-naphthyl)oxazolidine-2,4-dione in two crops [7.7 g.; m.p. 199°-201° C.; ir (KBr) 1820, 1740 cm-1 ].

Workup

  1. customRecrystallization from ethyl acetate/toluene
  2. customgave
  3. custompurified 5-(2-methoxy-1-naphthyl)oxazolidine-2,4-dione in two crops [7.7 g.; m.p. 199°-201° C.; ir (KBr) 1820, 1740 cm-1 ]

Sources & evidence

ORD record
ord-2f2b9e528be34e6cb52d03605431a24c
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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