Water → HCID 19041584, compound

HRID 1683879Notes

Reaction equation

HRID 1683879 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:17][CH2:16][C:8]2[C:9]3[CH:10]=[CH:11][NH:12][C:13]=3[CH:14]=[CH:15][C:7]=2[CH2:6]1)[CH2:2][CH3:3].ClS([N:25]=[C:26]=O)(=O)=O.CN(C)C=O.O>C(#N)C>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:17][CH2:16][C:8]2[C:9]3[C:10]([C:26]#[N:25])=[CH:11][NH:12][C:13]=3[CH:14]=[CH:15][C:7]=2[CH2:6]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 13342884HCID 13342884, compound

Product 1

HCID 19041584HCID 19041584, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To an ice-cold solution of di-n-propyl-(6,7,8,9-tetrahydro-3H-benzo[e]indol-7yl)amine, 9a (Chart 2) (180 mg, 0.67 mmol) in acetonitrile (5 mL) was added dropwise with a solution of chlorosufonyl isocyanate (60 mL, 0.68 mmol) in acetonitrile (1 mL) over 10 minutes. After stirring for 1 hour, dimethyl formamide (100 mL) was added and the reaction was stirred for an additional 2 hours. Water was added and extraction (dichloromethane) followed by evaporation of the combined organic extracts afforded 170 mg (86%) of the crude product. Purification on a silica column (hexane/ethyl acetate/methanol) afforded 45 mg (23%) of the pure material.

Workup

  1. stirringthe reaction was stirred for an additional 2 hours
  2. extractionextraction (dichloromethane)
  3. customfollowed by evaporation of the combined organic extracts
  4. customafforded 170 mg (86%) of the crude product
  5. customPurification on a silica column (hexane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-1c4a73861b824b56832f5e3a7e0a7d76
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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