Urea → 5,6,7,8-Tetrahydro-4H-oxazolo[4,5-d]azepin-2-ylamine

HRID 239121Notes

Reaction equation

HRID 239121 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].Br.Br[CH:7]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][C:8]1=O.[OH-].[Na+]>>[O:3]1[C:7]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][C:8]=2[N:1]=[C:2]1[NH2:4]

Participants

4

Reactant 3

HCID 1176UreaHCID 14798Sodium HydroxideHCID 226207665-Bromoazepan-4-one hydrobromide

Product 1

HCID 846497605,6,7,8-Tetrahydro-4H-oxazolo[4,5-d]azepin-2-ylamineYield 23.8%

Conditions

Temperature
70 °C

Procedure

6.6 g urea was added to 6 g 5-bromo-azepan-4-one hydrobromide. The mixture was stirred 24 h at 70° C. The reaction was basified with 4 N NaOH and extracted with chloroform and ethylacetate. The combined organic layers were evaporated to yield 800 mg of the desired product.

Workup

  1. extractionextracted with chloroform and ethylacetate
  2. customThe combined organic layers were evaporated

Sources & evidence

ORD record
ord-a80c10e05c5942e99a3af30a8d1cad82
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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