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

HRID 239171Notes

Reaction equation

HRID 239171 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-c93483b6efbc4b8aaedb56e7bd43aade
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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