Thiourea → 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-ylamine dihydrobromide

HRID 974284Notes

Reaction equation

HRID 974284 reaction equation
[BrH:1].[Br:2][CH:3]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5][C:4]1=O.[NH2:11][C:12]([NH2:14])=[S:13]>C(O)C>[BrH:2].[BrH:1].[NH2:14][C:12]1[S:13][C:4]2[CH2:5][CH2:6][NH:7][CH2:8][CH2:9][C:3]=2[N:11]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 226207665-Bromoazepan-4-one hydrobromide

Product 1

HCID 199857845,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-ylamine dihydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

214 g (0.78 mol) of 5-bromo-hexahydro-4H-azepin-4-one-hydrobromide are added to 59.7 g (0.78 mol) of thiourea in 1.6 1 of anhydrous ethanol, with stirring, at ambient temperature and the mixture is then refluxed for 3.5 hours. The reaction mixture is left to stand overnight, whilst being cooled with ice, and is filtered through a glass frit. The filter cake is washed with about 0.2 1 of ice cold ethanol and with about 0.2 1 of ether and then dried at 80° C. over calcium chloride in a circulating air dryer. Yield: 194 g (75% of theory), Melting point: 270°-280° C. (decomp.).

Workup

  1. temperaturethe mixture is then refluxed for 3.5 hours
  2. waitThe reaction mixture is left
  3. temperaturewhilst being cooled with ice
  4. filtrationis filtered through a glass frit
  5. washThe filter cake is washed with about 0.2 1 of ice cold ethanol and with about 0.2 1 of ether
  6. dry with materialdried at 80° C. over calcium chloride in a circulating air dryer

Sources & evidence

ORD record
ord-064661979af547fea726b252a7f9525f
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

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