1,4-Dibromobutane → HCID 13754417, compound

HRID 1462381Notes

Reaction equation

HRID 1462381 reaction equation
[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:4]=2[O:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>>[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([O:13][CH2:25][CH2:24][CH2:23][CH2:22][Br:21])[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

4

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 137543316-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

Product 1

HCID 13754417HCID 13754417, compound

Procedure

A suspension of 96.5 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one and 76 g of potassium carbonate in 300 ml of 1,4-dibromobutane is stirred for 5 hours in a bath at 120°-130°. The reaction mixture is filtered, and the excess 1,4-dibromobutane is distilled off at about 1 Torr. The crystalline residue is triturated with ether, and filtered off under suction. There is thus obtained crude 2,3-dihydro-2,2-dimethyl-6-(4-bromobutoxy)-4H-1,3-benzoxazin-4-one, m.p. 139°-142°, which is sufficiently pure for the further reaction.

Workup

  1. filtrationThe reaction mixture is filtered
  2. distillationthe excess 1,4-dibromobutane is distilled off at about 1 Torr
  3. customThe crystalline residue is triturated with ether
  4. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-4bcc39c8b2624daf88c84dec54a660be
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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