Toluene → HCID 20565232, compound

HRID 1413310Notes

Reaction equation

HRID 1413310 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 sufficient water to form 2 clear phases. 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. customThe organic phase is separated
  3. washwashed twice
  4. customAfter drying
  5. customevaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-50ae8dcdcb1044f39b887de381b85358
Source dataset
uspto-grants-1981_02
Patent number
US04249933

Reaction notes

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