HCID 21834217, compound → HCID 57203651, compound

HRID 1708994Notes

Reaction equation

HRID 1708994 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH:7]([C:10]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[O:11])[C:6]=2[CH:19]=1.N([O-])=[O:21].[Na+]>S(=O)(=O)(O)O.O>[OH:21][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH:7]([C:10]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[O:11])[C:6]=2[CH:19]=1

Participants

5

Reactant 2

HCID 21834217HCID 21834217, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57203651HCID 57203651, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent2×

Procedure

11.6 g of 5-amino-2,3-dihydro-N,N-dipropyl-3-benzothiophencarboxamide were dissolved in a mixture of 4 ml of conc. sulphuric acid and 40 ml of water. 3.1 g of sodium nitrite dissolved in 10 ml of water were added dropwise below 10° C. with stirring. After addition the mixture was stirred for further 0.5 hours. The diazonium solution was then added carefully to a pre-heated solution of 50 ml of conc. sulphuric acid in 40 ml of water at 115°-120° C. The resulting mixture was poured onto ice and subsequently extracted with dichloromethane. Yield of the title compound as a semicrystalline product: 8.7 g.

Workup

  1. additionwere added dropwise below 10° C.
  2. additionAfter addition the mixture
  3. stirringwas stirred for further 0.5 hours
  4. additionThe resulting mixture was poured onto ice
  5. extractionsubsequently extracted with dichloromethane

Sources & evidence

ORD record
ord-a4337253bd404ffd934c3c68591c4702
Source dataset
uspto-grants-1990_08
Patent number
US04946863

Reaction notes

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