Diethyl Ether → Hexyl isocyanate

HRID 1579001Notes

Reaction equation

HRID 1579001 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[O-:8][C:9]#[N:10].CN([S+](N(C)C)N(C)C)C.CCOCC>C(#N)C>[CH2:2]([N:10]=[C:9]=[O:8])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 81011-Bromohexane2×HCID 178486115HCID 178486115, compound

Product 1

HCID 75659Hexyl isocyanateYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromohexane, 3.3 g (0.02 mole), was added to a stirred solution of 6.2 g (0.03 mole) of tris(dimethylamino)sulfonium cyanate in 12 ml of acetonitrile at 25°. The course of the reaction was followed by glc analysis. One-half of the 1-bromohexane had reacted after 6 min., and the reaction was virtually complete after 2 hours. Ether, 20 ml, was added to the reaction mixture to precipitate dissolved salts, and the reaction mixture was filtered. Distillation of the filtrate gave 2.16 g (85%) of 1-hexyl isocyanate as a colorless liquid, b.p. 50°-51° (10 mm).

Workup

  1. customto precipitate
  2. dissolutiondissolved salts
  3. filtrationthe reaction mixture was filtered
  4. distillationDistillation of the filtrate

Sources & evidence

ORD record
ord-eaf4578d83d046769e17ecb49dacf015
Source dataset
uspto-grants-1976_02
Patent number
US03940402

Reaction notes

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