Cyanogen Bromide → HCID 13178282, compound

HRID 1074406Notes

Reaction equation

HRID 1074406 reaction equation
[H-].[Na+].[N:3]1[CH:4]=[CH:5][N:6]2[C:12](=[S:13])[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8][C:7]=12.[N:18]#[C:19]Br>O1CCCC1>[S:13]([C:12]1[N:6]2[CH:5]=[CH:4][N:3]=[C:7]2[S:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[N:11]=1)[C:19]#[N:18]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 13178255HCID 13178255, compound

Product 1

HCID 13178282HCID 13178282, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The starting material is prepared as follows: To the suspension of 1.44 g of 50% sodium hydride in mineral oil and 150 ml of dry tetrahydrofuran, 6.45 g of imidazo [2,1-b][1,3,5]benzothiadiazepin-5(6H)-thione are added in portions, and the mixture is stirred at room temperature under nitrogen for one hour. The resulting white suspension is cooled to 0° and the solution of 3.5 g of cyanogen bromide in 10 ml of tetrahydrofuran are added dropwise. The mixture is stirred at room temperature for 0.5 hour and evaporated. The residue is triturated with methylene chloride, the mixture washed with water, dried, concentrated to a small volume, washed with diethyl ether and filtered, to yield the 5-thiocyanatoimidazo[2,1-b][1,3,5]benzothiadiazepine melting at 111°-113°.

Workup

  1. customThe starting material is prepared
  2. additionare added in portions
  3. temperatureThe resulting white suspension is cooled to 0°
  4. stirringThe mixture is stirred at room temperature for 0.5 hour
  5. customevaporated
  6. customThe residue is triturated with methylene chloride
  7. washthe mixture washed with water
  8. customdried
  9. concentrationconcentrated to a small volume
  10. washwashed with diethyl ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-d60b8c7a8a9d456bb10ec905b284b25d
Source dataset
uspto-grants-1983_07
Patent number
US04391808

Reaction notes

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