Triethylamine → HCID 14402876, compound

HRID 1381822Notes

Reaction equation

HRID 1381822 reaction equation
O[CH2:2][N:3]1[C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]1=[O:16].C(N(CC)CC)C.S(Cl)([Cl:26])=O>C(Cl)(Cl)Cl>[Cl:26][CH2:2][N:3]1[C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]1=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 14402875HCID 14402875, compound

Product 1

HCID 14402876HCID 14402876, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-hydroxymethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (22.42 g) in chloroform (50 ml) is added a catalytic amount of triethylamine. The mixture is stirred at ambient temperature, treated dropwise with thionyl chloride, and stirred at 60° C. for 6 hours. The reaction mixture is made free form insoluble materials by filtration and the filtrate is poured into water. The separated chloroform layer is washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution successively, dried, and evaporated to obtain 4-chloromethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (17.23 g).

Workup

  1. stirringstirred at 60° C. for 6 hours
  2. filtrationby filtration
  3. additionthe filtrate is poured into water
  4. washThe separated chloroform layer is washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution successively
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-a81920d07f1a4e79a1e3223d8af71c15
Source dataset
uspto-grants-1989_02
Patent number
US04804394

Reaction notes

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