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

HRID 400474Notes

Reaction equation

HRID 400474 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 and heated 24 h at 70° C. 4 M aqueous sodium hydroxide was added and the mixture was extracted with chloroform and ethyl acetate. The combined organic layers were evaporated to give 800 mg of the desired product.

Workup

  1. extractionthe mixture was extracted with chloroform and ethyl acetate
  2. customThe combined organic layers were evaporated

Sources & evidence

ORD record
ord-6af43027edbd42c79986d672e086fb92
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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