Methyl isothiocyanate → 2'(N-methylthiocarbamyl)spiro[benzofuran-2(3H), 4'(2'H)-isoquinoline]

HRID 1758525Notes

Reaction equation

HRID 1758525 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:3][NH:2]1.[CH3:19][N:20]=[C:21]=[S:22]>C1C=CC=CC=1>[CH3:19][NH:20][C:21]([N:2]1[CH2:3][C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[S:22]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 15917444spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]

Product 1

HCID 132645342'(N-methylthiocarbamyl)spiro[benzofuran-2(3H), 4'(2'H)-isoquinoline]

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (5.0 g) in dry benzene (18 ml) is added methylisothiocyanate (3.1 g) in dry benzene (10 ml). After one hour, the product begins to separate. The mixture is stirred overnight and diluted with hexane (18 ml). The product is filtered, washed with hexane and dried to yield a solid. The solid is twice recrystallized from benzene to yield (3.0 g, 46%) as a solid, mp 165°.166°.

Workup

  1. customto separate
  2. additiondiluted with hexane (18 ml)
  3. filtrationThe product is filtered
  4. washwashed with hexane
  5. customdried
  6. customto yield a solid
  7. customThe solid is twice recrystallized from benzene
  8. customto yield (3.0 g, 46%) as a solid, mp 165°
  9. custom166°

Sources & evidence

ORD record
ord-b65e2fc82fe84c20bced951817e0ed73
Source dataset
uspto-grants-1983_02
Patent number
US04374137

Reaction notes

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