1-Bromo-3-chloropropane → 7-(3-chloropropoxy)-2H-1,4-benzoxazin-3(4H)-one

HRID 1381493Notes

Reaction equation

HRID 1381493 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].[Na]>C(OCCO)C>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 5360545SodiumHCID 100578707-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 133438727-(3-chloropropoxy)-2H-1,4-benzoxazin-3(4H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

7-Hydroxy-2H-1,4-benzoxazin-3(4H)-one was treated with 3-bromo-1-chloro-propane and sodium metal in ethyleneglycol monoethyl ether to give the desired product in 65% yield, mp 95° C.

Sources & evidence

ORD record
ord-c47d1240f9ce47ba82bc44d7d021c301
Source dataset
uspto-grants-1989_02
Patent number
US04803203

Reaction notes

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