Benzoyl chloride → HCID 11746637, compound

HRID 1698863Notes

Reaction equation

HRID 1698863 reaction equation
[S-:1][C:2]#[N:3].[NH4+].C(Cl)(=O)C1C=CC=CC=1.[NH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[CH2:21][CH2:20][CH2:19][CH2:18]2.[OH-].[NH4+]>CC(C)=O.C(O)C>[CH3:26][O:25][C:24]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:16][C:15]=1[NH:14][C:2]([NH2:3])=[S:1]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 15666Ammonium thiocyanateHCID 5957423-Methoxy-5,6,7,8-tetrahydro-naphthalen-2-ylamine2×

Product 1

HCID 11746637HCID 11746637, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 702EthanolSolvent

Procedure

1.45 g of ammonium thiocyanate are dissolved in 30 ml of acetone and after 2.2 ml of benzoyl chloride have been added, the reaction mixture is heated under reflux for 15 minutes. 2.6 g of 6-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene (Compound 4-1) dissolved in 20 ml of acetone are added and then the mixture is heated under reflux for 30 minutes. It is evaporated to dryness, the residue obtained is taken up in a minimum of ethanol, 50 ml of 30% ammonium hydroxide are added and the mixture is heated under reflux for 20 hours. The thiourea obtained is cooled, filtered, washed with waer and then with an ethyl acetate/hexane 25/75 (v/v) mixture. 2.8 g of the expected product are obtained in the form of a beige powder; yield=80%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. additionare added
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 30 minutes
  6. customIt is evaporated to dryness
  7. customthe residue obtained
  8. additionare added
  9. temperaturethe mixture is heated
  10. temperatureunder reflux for 20 hours

Sources & evidence

ORD record
ord-1ea6bcddaa0e44fbbaaa774e76555394
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

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