1,1'-Thiocarbonyldiimidazole → HCID 86633742, compound

HRID 415533Notes

Reaction equation

HRID 415533 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:25])([CH3:24])[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:26](N1C=CN=C1)(N1C=CN=C1)=[S:27]>C(Cl)Cl>[CH3:24][C:14]([CH3:25])([CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[NH:1][C:26]1=[S:27])[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 66620426HCID 66620426, compound

Product 1

HCID 86633742HCID 86633742, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-[(3-aminoquinolin-4-yl)amino]-2,2-dimethylpropylcarbamate (7.16 g, 20.8 mmol) was suspended in 200 mL of CH2Cl2 and treated with 1,1′-thiocarbonyldiimidazole (4.07 g, 22.9 mmol) under an atmosphere of N2. After about 2 hours a precipitate had formed. It was isolated by filtration and dried under vacuum to afford tert-butyl 2,2-dimethyl-3-(2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (7.78 g) as a white solid.

Workup

  1. customAfter about 2 hours a precipitate had formed
  2. customIt was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-cf57810d82764439ae84e17798e80dea
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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