Carbon Tetrachloride → HCID 21454910, compound

HRID 436004Notes

Reaction equation

HRID 436004 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([NH:14][CH:15]1[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]1[CH2:17]4)[CH2:21]3)=S)[CH2:8]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.[NH:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>C1(C)C=CC=CC=1.C(O)(C)(C)C.C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1)=[N:14][CH:15]1[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]1[CH2:17]4)[CH2:21]3)[CH2:8]2

Participants

9

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8083MorpholineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 21454912HCID 21454912, compound

Product 1

HCID 21454910HCID 21454910, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of 3.45 g. (0.01 mole) of N,N'-di-2-adamantylthiourea, 3.15 g. (0.012 mole) of triphenylphosphine, 1.55 g. (0.01 mole) of carbon tetrachloride and 1.0 g. (0.01 mole) of triethylamine in 25 ml. of methylene chloride is stirred at 40°-45° for 2.5 hr. The solvent is evaporated and the residue which contained N,N'-di-2-adamantylcarbodiimide is reacted with 10 ml. of morpholine in 10 ml. of tert-butyl alcohol on a steam-bath for 16 hrs. The mixture is diluted with toluene and evaporated in vacuo to remove excess morpholine. The residue is partitioned between 10 percent hydrochloric acid and ether. Some solid insoluble in both phases is filtered off and discarded. The acid layer is combined with the water extracts of the ether layer. The acid layer is basified with 20 percent sodium hydroxide to pH 13-14 and nitrogen bubbled through the solution to remove ether. The solid which separated is collected, washed with water, airdried and recrystallized from isopropanol-water: 1.6 (40 percent), m.p. 123-124.

Workup

  1. additionA mixture of 3.45 g
  2. customThe solvent is evaporated
  3. customis reacted with 10 ml
  4. customevaporated in vacuo
  5. customto remove excess morpholine
  6. customThe residue is partitioned between 10 percent hydrochloric acid and ether
  7. filtrationSome solid insoluble in both phases is filtered off
  8. custombubbled through the solution
  9. customto remove ether
  10. customThe solid which separated
  11. customis collected
  12. washwashed with water
  13. customrecrystallized from isopropanol-water

Sources & evidence

ORD record
ord-951698103eb14d99825e52fbd22f481f
Source dataset
uspto-grants-1977_02
Patent number
US04007181

Reaction notes

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