Ethyl 2-isothiocyanatobenzoate → HCID 14013538, compound

HRID 1904856Notes

Reaction equation

HRID 1904856 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][NH2:25])[CH2:19][CH2:18]1.[N:26]([C:29]1[CH:39]=[CH:38][CH:37]=[CH:36][C:30]=1[C:31](OCC)=[O:32])=[C:27]=[S:28]>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]2[C:31](=[O:32])[C:30]3[C:29](=[CH:39][CH:38]=[CH:37][CH:36]=3)[NH:26][C:27]2=[S:28])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 523235Ethyl 2-isothiocyanatobenzoateHCID 14013481HCID 14013481, compound

Product 1

HCID 14013538HCID 14013538, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 5.1 parts of 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidineethanamine and 270 parts of tetrahydrofuran was added dropwise a solution of 3.8 parts of ethyl 2-isothiocyanatobenzoate in tetrahydrofuran. Upon completion, stirring was continued for 1 hour. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 1.4 parts (18.6%) of 3-[2-[4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidinyl]ethyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinone; mp. 192.0° C. (492).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from 2-propanone
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-391d401330ab4409a11613b1a68f092f
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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