Carbon Tetrachloride → HCID 9996696, compound

HRID 1657575Notes

Reaction equation

HRID 1657575 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=S)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:37].C(N(CC)CC)C.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>C(O)(C)(C)C.C(Cl)Cl>[ClH:37].[CH:1]1([NH:7][C:8]([N:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)=[N:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8083MorpholineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 727200Dicyclohexylthiourea

Product 1

HCID 9996696HCID 9996696, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of 2.4 gm. (0.01 mole) of N,N'-dicyclohexylthiourea, 3.15 gm. (0.012 mole) of triphenylphosphine, 1.55 gm. (0.01 mole) of carbon tetrachloride, and 1.0 gm. (0.01 mole) of triethylamine in 25 ml. of methylene chloride is stirred for 2.5 hr. at 40°-45°. The reaction mixture is concentrated and the residue extracted several times with hot Skellysolve B. The combined Skellysolve B extracts are cooled to room temperature, filtered and evaporated. The crude N,N'-dicyclohexylcarbodiimide is reacted with 5 ml. of morpholine in 10 ml of tert-butyl alcohol at reflux for 16 hours. The reaction mixture is evaporated, toluene added and concentrated to remove residual morpholine. The residue is partitioned between ether and 10% hydrochloric acid. The acid layer is basified with 20% sodium hydroxide solution, nitrogen bubbled through the solution to remove ether and cooled at 5°. The product is collected, 2.07 gm. (70%), m.p. 105°-107°. The HCl salt is prepared and recrystallized from acetonitrile-ether, m.p. 226°-227°.

Workup

  1. additionA mixture of 2.4 gm
  2. customat 40°-45°
  3. concentrationThe reaction mixture is concentrated
  4. extractionthe residue extracted several times with hot Skellysolve B
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude N,N'-dicyclohexylcarbodiimide is reacted with 5 ml
  8. customThe reaction mixture is evaporated
  9. additiontoluene added
  10. concentrationconcentrated
  11. customto remove residual morpholine
  12. customThe residue is partitioned between ether and 10% hydrochloric acid
  13. custombubbled through the solution
  14. customto remove ether
  15. temperaturecooled at 5°
  16. customThe product is collected
  17. customrecrystallized from acetonitrile-ether, m.p. 226°-227°

Sources & evidence

ORD record
ord-de28eb34e2894a0aab57759803beea8d
Source dataset
uspto-grants-1976_06
Patent number
US03961056

Reaction notes

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