Sodium Hydroxide → HCID 13645514, compound

HRID 1111122Notes

Reaction equation

HRID 1111122 reaction equation
[CH3:1][C:2]1[N:3]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:4]2[C:9]([C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[N-:28]=[C:29]=[O:30].[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[N:3]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:4]2[C:9]([C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:29](=[O:30])[NH2:28])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11051568NaNCOHCID 13645496HCID 13645496, compound

Product 1

HCID 13645514HCID 13645514, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a stirred suspension of 12.0 g. (0.03 mole) of 2-methyl-3-(4-aminobenzoyl)-1-[2-(4-morpholinyl)ethyl]- 1H-indole (Example 4B) in 15 ml of glacial acetic acid and 30 ml. of water was added a solution of 4.5 g. (0.06 mole) of sodium isocyanate in 30 ml of water. The mixture was stirred at room temperature for two hours, then diluted with water and made alkaline with 10% sodium hydroxide The solid which separated was collected and recrystallized from DMF to give 5.9 g (48%) of 2-methyl3-(4-carbamylaminobenzoyl)-1-[2-(4-morpholinyl)ethyl]-1H-indole, m p. 192°-202° C.

Workup

  1. additionTo a stirred suspension of 12.0 g
  2. customseparated
  3. customwas collected
  4. customrecrystallized from DMF

Sources & evidence

ORD record
ord-4517a4a6dcbf445e99b6a379e4c267aa
Source dataset
uspto-grants-1990_12
Patent number
US04978664

Reaction notes

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