Toluene → HCID 20565232, compound

HRID 848399Notes

Reaction equation

HRID 848399 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].C1(C)C=CC=CC=1.[CH3:14][C:15]1([CH3:21])[CH2:20][CH2:19][O:18][CH2:17][NH:16]1.C(N(CC)CC)C>O.C(Cl)Cl>[Cl:1][CH:2]([Cl:6])[C:3]([N:16]1[C:15]([CH3:21])([CH3:14])[CH2:20][CH2:19][O:18][CH2:17]1)=[O:4]

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 20565235HCID 20565235, compound

Product 1

HCID 20565232HCID 20565232, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

At -10° C. and while stirring, 23.2 parts by weight of dichloroacetyl chloride in 100 parts by volume of toluene is dripped into 23.0 parts by weight of 4,4-dimethyltetrahydro-1,3-oxazine and 20.7 parts by weight of triethylamine in 100 parts by volume of toluene. After the mixture has been stirred for 2 hours at room temperature, there are added 150 parts by volume of methylene chloride and enough water for 2 clear phases to be formed. The organic phase is separated and washed twice, each time with 50 parts by volume of water. After drying and evaporation of the solvents under reduced pressure, there is isolated 41 parts by weight of N-dichloroacetyl-4,4-dimethyltetrahydro-1,3-oxazine of melting point 105°-106° C., which melts, after recrystallization from methanol, at 106°-107° C.

Workup

  1. stirringAfter the mixture has been stirred for 2 hours at room temperature
  2. customto be formed
  3. customThe organic phase is separated
  4. washwashed twice
  5. customAfter drying
  6. customevaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-3696f723948f4e91853cabd105a5791e
Source dataset
uspto-grants-1981_10
Patent number
US04295875

Reaction notes

Loading…