Trichloroacetic Acid → 2-[2-(bis-(2-chloroethyl)-amino)-6-methyl-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt

HRID 1731967Notes

Reaction equation

HRID 1731967 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:14][CH2:15][Cl:16])[P:5]1(=[O:13])[NH:10][CH:9](O)[CH2:8][CH:7]([CH3:12])[O:6]1.[CH:17]1([NH3+:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[SH:24][CH2:25][CH2:26][S:27]([O-:30])(=[O:29])=[O:28].ClC(Cl)(Cl)C(O)=O>O.CC(C)=O>[CH:17]1([NH3+:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl:1][CH2:2][CH2:3][N:4]([CH2:14][CH2:15][Cl:16])[P:5]1(=[O:13])[NH:10][CH:9]([S:24][CH2:25][CH2:26][S:27]([O-:30])(=[O:29])=[O:28])[CH2:8][CH:7]([CH3:12])[O:6]1

Participants

6

Reactant 3

HCID 6421Trichloroacetic AcidHCID 230498732-Sulfanylethane-1-sulfonic acid--cyclohexanamine (1/1)HCID 230498752-(bis-(2-chloroethyl)-amino)-4-hydroxy-6-methyl-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide

Product 1

HCID 1317149752-[2-(bis-(2-chloroethyl)-amino)-6-methyl-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1.45 g (5 mmol) of 2-(bis-(2-chloroethyl)-amino)-4-hydroxy-6-methyl-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide and 1.2 g (5 mmol) of cyclohexylammonium-2-mercaptoethanesulphonate were dissolved in 5 ml of water and in 5 ml of acetone, acidified with trichloroacetic acid and left to stand for 20 hours at 0° C. The mixture was then filtered, the filtrate was carefully concentrated under vacuum, the residue was taken up twice in acetone and was concentrated. The residue was then dissolved in acetone, precipitated with ether, and washed with ether and dried.

Workup

  1. waitleft
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was carefully concentrated under vacuum
  4. concentrationwas concentrated
  5. dissolutionThe residue was then dissolved in acetone
  6. customprecipitated with ether
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-350e79586f1941ef8f389983802a67bf
Source dataset
uspto-grants-1986_11
Patent number
US04623742

Reaction notes

Loading…