Phenyl isocyanate → N-(phenylcarbamyloxy)-2-methyl-2-phenyl-4-trichloromethyl-5,5-dichloro-6-oxotetrahydro-1,3-oxazine

HRID 26692Notes

Reaction equation

HRID 26692 reaction equation
[OH:1][N:2]1[CH:7]([C:8]([Cl:11])([Cl:10])[Cl:9])[C:6]([Cl:13])([Cl:12])[C:5](=[O:14])[O:4][C:3]1([CH3:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(N(CC)CC)C.ClCCl>[C:22]1([NH:28][C:29]([O:1][N:2]2[CH:7]([C:8]([Cl:9])([Cl:10])[Cl:11])[C:6]([Cl:13])([Cl:12])[C:5](=[O:14])[O:4][C:3]2([CH3:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 21322128N-hydroxy-2-methyl-2-phenyl-4-trichloromethyl-5,5-dichloro-6-oxotetrahydro-1,3-oxazine

Product 1

HCID 21322127N-(phenylcarbamyloxy)-2-methyl-2-phenyl-4-trichloromethyl-5,5-dichloro-6-oxotetrahydro-1,3-oxazineYield 39%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 8 g (0.02 mol) N-hydroxy-2-methyl-2-phenyl-4-trichloromethyl-5,5-dichloro-6-oxotetrahydro-1,3-oxazine, 2.4 g (0.02 mol) phenylisocyanate and several drops triethylamine in 90 ml dichloromethane was stirred at about 10° C. for about 2 days. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give a yellow oil. The oil crystallized from ethanol/hexane to give 4 g of product, m.p. 154°-157° C. The product is tabulated in Table I as Compound No. 8.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customto give a yellow oil
  4. customThe oil crystallized from ethanol/hexane

Sources & evidence

ORD record
ord-e99868daabbf4ff2a4cdcb3104c95ef8
Source dataset
uspto-grants-1979_04
Patent number
US04151279

Reaction notes

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