Dichloromethane → HCID 15618732, compound

HRID 2379777Notes

Reaction equation

HRID 2379777 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1.[C-:12]#[N:13].[Na+].C(Cl)Cl>CS(C)=O>[C:12]([CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)#[N:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 1843482-Chloromethylbenzofuran

Product 1

HCID 15618732HCID 15618732, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound 5 (117 g) was added dropwise to a stirring suspension of sodium cyanide (37.64 g) in dimethyl sulfoxide (100 ml). The reactor was placed from time to time into an ice bath in order to keep the reaction temperature between 20° C. and 45° C. Addition lasted 60 minutes. The reaction mixture was stirred for another 16 hours, then poured into methylene chloride (500 ml), washed with water (500 ml, then 2×250 ml), and evaporated to dryness. A small sample was purified on a silica gel column, eluting with dichloromethane/hexanes (50:50 v/v).

Workup

  1. customThe reactor was placed from time to time into an ice bath in order
  2. customthe reaction temperature between 20° C. and 45° C
  3. additionAddition
  4. washwashed with water (500 ml
  5. custom2×250 ml), and evaporated to dryness
  6. customA small sample was purified on a silica gel column
  7. washeluting with dichloromethane/hexanes (50:50 v/v)

Sources & evidence

ORD record
ord-9705657e36b94fb482f37ef1063598ac
Source dataset
uspto-grants-1994_11
Patent number
US05364880

Reaction notes

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