Thionyldiimidazole → 5-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxamide

HRID 2166360Notes

Reaction equation

HRID 2166360 reaction equation
[O:1]([C:8]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:9]=1[C:10]1[C:11]([CH2:24][O:25][CH3:26])=[C:12]([C:21](O)=[O:22])[N:13]=[CH:14][C:15]=1[NH:16]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1NC=CN=1)(C1[NH:30]C=CN=1)=O>O1CCCC1>[O:1]([C:8]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:9]=1[C:10]1[C:11]([CH2:24][O:25][CH3:26])=[C:12]([C:21]([NH2:30])=[O:22])[N:13]=[CH:14][C:15]=1[NH:16]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21946057ThionyldiimidazoleHCID 230394415-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid

Product 1

HCID 230394095-Phenoxy-4-methoxymethyl-beta-carboline-3-carboxamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.7 g of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxylic acid is added to a solution of 30 mmol of thionyldiimidazole in 150 ml of tetrahydrofuran. The reaction mixture is stirred for 5 hours and filtered. The filtrate is mixed with 12 ml of 25% NH3 in water, stirred overnight and concentrated in a vacuum to 50 ml. After addition of 100 ml of water, 2 g of the desired product is obtained as yellow crystals.

Workup

  1. filtrationfiltered
  2. additionThe filtrate is mixed with 12 ml of 25% NH3 in water
  3. stirringstirred overnight
  4. concentrationconcentrated in a vacuum to 50 ml
  5. additionAfter addition of 100 ml of water

Sources & evidence

ORD record
ord-9d4c122f73f64cb28561a935199ed171
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

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