Sodium Carbonate → HCID 53952014, compound

HRID 1533993Notes

Reaction equation

HRID 1533993 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[CH:21][NH:22]2)=[O:17])([CH3:4])[CH3:3].[Cl:27]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH3:4][C:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20]([Cl:27])=[CH:21][NH:22]2)=[O:17])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31398ChlorosuccinimideHCID 3077190HCID 3077190, compound

Product 1

HCID 53952014HCID 53952014, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.3 g of [2-[3-[(1,1-dimethylethyl)-amino]-propoxy]-phenyl]-(1H-indol-4-yl) methanone of Step F of Example 3 in 50 ml of acetic acid in the presence of 2.64 g of N-chloro succinimide was stirred for 2 hours at ambient temperature and was then poured into 300 ml of saturated aqueous solution of sodium carbonate and extracted with ethyl acetate. The organic phase was washed with salt water, dried and concentrated to dryness. After chromatography of the residue on silica (eluant:ethyl acetate triethylamine 95-5), 5.52 g of the expected product were obtained and was used as is for the following step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with salt water
  3. customdried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7aea540fc66f40bcbe03944dcba89d2b
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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