1-Isocyanato-4-methoxybenzene → HCID 21510705, compound

HRID 1576482Notes

Reaction equation

HRID 1576482 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH2:3]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1>C1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([O:1][CH:2]2[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][CH:10]=3)[CH2:3]2)=[O:28])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 21510684HCID 21510684, compound

Product 1

HCID 21510705HCID 21510705, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A stirred suspension of 3.5 g. (0.015 mole) of 3-[2-(3-hydroxypyrrolidinyl)ethyl]indole in 50 ml. of dry benzene was treated dropwise with 2.3 g. (0.015 mole) of p-methoxyphenylisocyanate in 15 ml. of dry benzene. After addition (0.5 hour) the mixture was refluxed for 12 hours after which time only a small amount of solid remained suspended. The residue was filtered off and the filtrate was evaporated under vacuum to an orange gum. The product was dissolved in benzene and chromatographed on 200 g. of 60-100 mesh magnesium silicate, eluting first with benzene then benzene with increasing amounts of acetone. At 20% acetone-benzene pure product was obtained from the column; yield 3.5 g. (60%). The glassy solid would not crystallize.

Workup

  1. additionA stirred suspension of 3.5 g
  2. additionAfter addition (0.5 hour) the mixture
  3. temperaturewas refluxed for 12 hours after which time only a small amount of solid
  4. filtrationThe residue was filtered off
  5. customthe filtrate was evaporated under vacuum to an orange gum
  6. dissolutionThe product was dissolved in benzene
  7. customchromatographed on 200 g
  8. washof 60-100 mesh magnesium silicate, eluting first with benzene
  9. customAt 20% acetone-benzene pure product was obtained from the column
  10. customThe glassy solid would not crystallize

Sources & evidence

ORD record
ord-fc54e1ed02f1410ea54b36b502b01de4
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

Loading…