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

HRID 648101Notes

Reaction equation

HRID 648101 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°-166°

Sources & evidence

ORD record
ord-bb5a4a3675f1429fb47bd959d80e1577
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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