Methyl chloroformate → HCID 21191848, compound

HRID 1069550Notes

Reaction equation

HRID 1069550 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12](O)=[O:13])=[CH:8][CH:7]=[C:6]([CH3:15])[CH:5]=2.ClC(OC)=O.C([N:30](CC)CC)C>>[CH3:1][C:2]1[N:3]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([NH2:30])=[O:13])=[CH:8][CH:7]=[C:6]([CH3:15])[CH:5]=2

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 21191875HCID 21191875, compound

Product 1

HCID 21191848HCID 21191848, compoundYield 39%

Procedure

A solution of 0.48 g (1.64 mmol) of 2,6-dimethyl-1-(phenylmethyl)-1H-indole-3-acetic acid in 25 ml of tetrahydrofuran(THF) was cooled with an ice-water bath, 0.45 ml of triethylamine was added followed by 0.13 ml (1.7 mmol) of methyl chloroformate. After 0.5 hour, gaseous NH3 was bubbled into the reaction mixture for 0.5 hour, the cooling bath removed and the mixture stirred for 2 hours. It was then poured into water and extracted with EtOAc, the EtOAc solution washed with a Na2CO3 solution, dried(Na2SO4), and concentrated at reduced pressure. The residue was crystallized from MeOH/water, to give 0.19 g (39% yield) of 2,6-dimethyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 160-163° C.

Workup

  1. customgaseous NH3 was bubbled into the reaction mixture for 0.5 hour
  2. customthe cooling bath removed
  3. additionIt was then poured into water
  4. extractionextracted with EtOAc
  5. washthe EtOAc solution washed with a Na2CO3 solution, dried(Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was crystallized from MeOH/water

Sources & evidence

ORD record
ord-7949e69e6ca64136bbc3da9721cd660f
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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