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

HRID 1731968Notes

Reaction equation

HRID 1731968 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[CH:9](O)[CH2:8][CH2:7][O:6][P:5]1(=[O:15])[NH:11][CH2:12][CH2:13][Cl:14].[CH:16]1([NH3+:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[SH:23][CH2:24][CH2:25][S:26]([O-:29])(=[O:28])=[O:27].ClC(Cl)(Cl)C(O)=O>O>[CH:16]1([NH3+:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl:1][CH2:2][CH2:3][N:4]1[CH:9]([S:23][CH2:24][CH2:25][S:26]([O-:29])(=[O:28])=[O:27])[CH2:8][CH2:7][O:6][P:5]1([NH:11][CH2:12][CH2:13][Cl:14])=[O:15]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 3081714-HydroxyifosfamideHCID 230498732-Sulfanylethane-1-sulfonic acid--cyclohexanamine (1/1)

Product 1

HCID 1317149762-[3-(2-chloroethyl)-2-(2-chloroethylamino)-2-oxo-tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl-thio]-ethanesulphonic acid cyclohexylammonium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

277 mg (1 mmol) of 3-(2-chloroethyl)-2-(2-chloroethylamino)-hydroxy-tetrahydro-2H-1,3,2-oxazaphosphorin-2oxide and 240 mg (1 mmol) of cyclohexylammonium-2-mercaptoethanesulphonate were dissolved in 4 ml of water, mixed with a trace of trichloroacetic acid and stored for 20 hours at 0° C. The reaction mixture which was concentrated under vacuum was dissolved twice in ethanol and re-concentrated. It was then taken up in ethanol and precipitated with ether.

Workup

  1. concentrationThe reaction mixture which was concentrated under vacuum
  2. dissolutionwas dissolved twice in ethanol
  3. concentrationre-concentrated
  4. customprecipitated with ether

Sources & evidence

ORD record
ord-5daf838221fe4e26ac768c07f3e92831
Source dataset
uspto-grants-1986_11
Patent number
US04623742

Reaction notes

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