Ethyl Acetate → HCID 14324465, compound

HRID 728527Notes

Reaction equation

HRID 728527 reaction equation
[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16](O)=[O:17])=[CH:12][C:11]=2[N+:19]([O-:21])=[O:20])[C:7](=[O:22])[C:6]=1[CH2:23][Cl:24])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C(OC(Cl)=O)C.[CH2:37]([NH2:53])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>O.C(N(CC)CC)C>[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:17])[NH:53][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:12][C:11]=2[N+:19]([O-:21])=[O:20])[C:7](=[O:22])[C:6]=1[CH2:23][Cl:24])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8926HexadecylamineHCID 10928Ethyl chloroformateHCID 14324458HCID 14324458, compound

Product 1

HCID 14324465HCID 14324465, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-15 °C

Procedure

81.6 g of 5-t-butyl-4-chloromethyl-2-(4-carboxy-2-nitrophenyl)-4-isooxazolin-3-one was mixed with 480 ml of ethyl acetate, and cooled to -15° C. To the thus obtained suspension, 32.6 ml of triethylamine was added dropwise, and then 22.0 ml of ethylchlorocarbanate was further added dropwise as the reaction mixture was kept at -10° C. After running the reaction for 50 minutes, 49 g of hexadecylamine was added to the reaction mixture to further undergo the reaction for 10 minutes at -10° C. The temperature of the reaction system was gradually raised up to room temperature. The resulting reaction mixture was allowed to stand overnight, and then 400 ml of water was added thereto to separate into two phases. The organic phase was taken out, and concentrated to dryness. The residue was crystallized from methanol. Yield: 100.9 g, Percent yield: 75.9%.

Workup

  1. customwas kept at -10° C
  2. customthe reaction for 50 minutes
  3. customthe reaction for 10 minutes at -10° C
  4. temperatureThe temperature of the reaction system was gradually raised up to room temperature
  5. customThe resulting reaction mixture
  6. customto separate into two phases
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-39dbad56a7f04e9797100ac23995fce2
Source dataset
uspto-grants-1991_09
Patent number
US05049477

Reaction notes

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