Phosgene → HCID 21389343, compound

HRID 1833413Notes

Reaction equation

HRID 1833413 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])C)(C)C.C([Li])CCC.[CH3:13][CH:14]([N:16]=[C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH3:15].C(Cl)(Cl)=[O:24].[CH3:27][CH2:28][CH2:29][CH2:30][CH2:31]C>C1C=CC=CC=1.O.C(#N)C1C=CC=CC=1>[CH:14]([N:16]1[C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[C:5]([C:7]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:4][C:1]1=[O:24])([CH3:15])[CH3:13]

Participants

9

Reactant 5

HCID 6371PhosgeneHCID 7912DiisopropylamineHCID 8058HexaneHCID 637899HCID 637899, compoundHCID 178418339Butyllithium

Product 1

HCID 21389343HCID 21389343, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 7505BenzonitrileSolvent

Procedure

To 5.05 g. diisopropylamine in 50 ml. dry benzene is added butyl lithium (31.5 ml. of a 1.6N solution in hexane). After 15 minutes, 7.65 g. of 1-methyl-N-(cyclohexylidene)-ethylamine prepared as in Example 1 is added during about 2 minutes. 5.5 g. benzonitrile is added after 10 minutes to give a deep red solution, and after a further 10 minutes about 5 ml. of water are added, causing the color to change to pale yellow. After 30 minutes, 5 g. of phosgene in a 12.5% solution in benzene is added dropwise to this mixture at 0°. After 1 hour, the reaction was worked up as in Example 1 to give the same product.

Workup

  1. additionis added during about 2 minutes
  2. customto give a deep red solution
  3. waitafter a further 10 minutes about 5 ml
  4. waitAfter 30 minutes
  5. waitAfter 1 hour
  6. customto give the same product

Sources & evidence

ORD record
ord-7a81764c66d847afa71b787d54a09569
Source dataset
uspto-grants-1978_01
Patent number
US04066665

Reaction notes

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