Dodecanoyl chloride → 4-(Dodecanoyloxymethyl)-4-methyloxazolidin-2-one

HRID 1087765Notes

Reaction equation

HRID 1087765 reaction equation
[OH:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C(N(CC)CC)C.[C:17](Cl)(=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>ClCCl>[C:17]([O:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1)(=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 245546Nsc57599

Product 1

HCID 148362314-(Dodecanoyloxymethyl)-4-methyloxazolidin-2-oneYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.5 g of 2-amino-2-methyl-1,3-propanediol and 12.3 g of diethyl carbonate, 0.5 g of sodium ethoxide in 100 ml of toluene was refluxed for 20 hours, cooled and concentrated at reduced pressure to give 13.6 g of crude product. Recrystallization from ethanol gave 9.23 g (67%) of4-hydroxymethyl-4-methyloxazolidin-2-one, m.p. 115 C. To a solution of 2.62 g of 4-hydroxymethyl-4-methyloxazolidin-2-one and 5 ml of triethylamine in 100 ml of dichloromethane was added dropwise 4.6 g of dodecanoyl chloride in 10 ml of dichloromethane. After 3 hours at room temperature the reaction mixture was concentrated, the residue was taken up in ether and washed with aqueous sodium bicarbonate. The ether layer was dried and concentrated to give 4.33 g (69%) of a thick yellow oil. Recrystallization from dichloromethane/hexane (1:10) gave 2.73 g (45%) of white crystals, m.p. 53-55 C.

Workup

  1. concentrationAfter 3 hours at room temperature the reaction mixture was concentrated
  2. washwashed with aqueous sodium bicarbonate
  3. dry with materialThe ether layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-841fc62497264b729448d5200cf787d8
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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