Methyl Isocyanate → HCID 22627322, compound

HRID 278122Notes

Reaction equation

HRID 278122 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[C:7]([CH2:19][CH2:20][CH3:21])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:4][CH:3]=1.[CH3:27][N:28]=[C:29]=[O:30]>C(Cl)(Cl)Cl>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:29]([NH:28][CH3:27])=[O:30])[CH:10]=2)[C:6]([C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[C:7]1[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 22627183HCID 22627183, compound

Product 1

HCID 22627322HCID 22627322, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 6-amino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole (100 mg) in chloroform (2 ml) was added methylisocyanate (0.5 ml) at 0° C. The reaction mixture was stirred at 20° C. for 1 hour, then evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:1) to give crystals which were recrystallized from a mixture of ethyl acetate and hexane to give 1-(2-chlorobenzyl)-3-isobutyryl-6-(3-methylureido)-2-propylindole (75 mg) as colorless crystals.

Workup

  1. customevaporated
  2. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:1)
  3. customto give crystals which
  4. customwere recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5aa2d8f34bea4515b4c8ef614cdf016f
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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