Dimethylformamide → 6-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione

HRID 1611872Notes

Reaction equation

HRID 1611872 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[NH:8][C:7](=[O:12])[C:6]=2[CH:13]=1.CN(C=O)C.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(N(C(C)C)CC)(C)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[N:8]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])[C:7](=[O:12])[C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 81531DiisopropylethylamineHCID 903596-Chloro-2h-1,3-benzoxazine-2,4(3h)-dioneHCID 2214831,10-Dibromodecane

Product 1

HCID 222514226-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dioneYield 49.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of 9.77 g of 6-chloro-2H-1,3-benzoxazine-2,4(3H)-dione (50 mmol) and 60 ml of DMF was treated with a solution of 1,10-dibromodecane (52.52 g, 0.175 mol) and DMF (60 ml) was added. Diisopropylethylamine (9.6 ml, 55 mmol) was added dropwise. A thermometer and condenser were attached, and the flask was placed in an oil bath. The reaction was heated to 60 C for approximately 3 hrs, cooled to 47 C and hexanes (150 ml) were added. The mixture was diluted with water (175 ml). The resulting solids were removed by filtration. The aqueous layer was washed with warm hexanes. The resulting solids were filtered from the hexane layer and recrystallized from warm hexanes to give 10.39 g of 6-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione.

Workup

  1. additionwas added
  2. customthe flask was placed in an oil bath
  3. temperatureThe reaction was heated to 60 C for approximately 3 hrs
  4. additionwere added
  5. customThe resulting solids were removed by filtration
  6. washThe aqueous layer was washed with warm hexanes
  7. filtrationThe resulting solids were filtered from the hexane layer
  8. customrecrystallized
  9. temperaturefrom warm hexanes

Sources & evidence

ORD record
ord-679dd726efbf463f843aea8d41ee732c
Source dataset
uspto-grants-2006_01
Patent number
US06991798B1

Reaction notes

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