Aminoglutethimide → 2-Thenylamine, N,N-bis(2-chloroethyl)-, hydrochloride

HRID 2280045Notes

Reaction equation

HRID 2280045 reaction equation
[CH:1]1[CH:5]=[C:4]([CH2:6][N:7]([CH2:11][CH2:12][Cl:13])[CH2:8][CH2:9][Cl:10])[S:3][CH:2]=1.[ClH:14].[Br-].CN(C=O)C.C(N(CC)CC)C.CCC1(C2C=CC(N)=CC=2)C(=O)NC(=O)CC1>O>[CH:1]1[CH:5]=[C:4]([CH2:6][N:7]([CH2:11][CH2:12][Cl:13])[CH2:8][CH2:9][Cl:10])[S:3][CH:2]=1.[ClH:14]

Participants

6

Reactant 4

HCID 2145AminoglutethimideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 131715389HCID 131715389, compound

Product 1

HCID 2036042-Thenylamine, N,N-bis(2-chloroethyl)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One milimole of DCTA-bromide was added to 5 ml of 50% DMF containing 0.2 ml of 2,3-dithioethylene and 0.5 ml of triethylamine. The mixture was incubated under argon for 2 hours at 60-70° C. The solution was then mixed with 20 ml of water and loaded onto a Dowex AG-1 column of 9 ml bed volume. The column was washed with 50 ml of 0.1M acetic acid solution until the flowthrough was thiol free. The DCTA-SH was then eluted with 0.25M HCl. The thiol containing fractions were combined, evaporated to dryness under reduced pressure at 40° C. and the free acid (300 mg) was stored at −20° C. under argon.

Workup

  1. washThe column was washed with 50 ml of 0.1M acetic acid solution until the flowthrough
  2. washThe DCTA-SH was then eluted with 0.25M HCl
  3. customevaporated to dryness under reduced pressure at 40° C.
  4. customwas stored at −20° C. under argon

Sources & evidence

ORD record
ord-75f2e04a6d504bde8e6120813f45006f
Source dataset
uspto-grants-2015_09
Patent number
US09134302B2

Reaction notes

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