Ethanethiol → HCID 54120511, compound

HRID 1448430Notes

Reaction equation

HRID 1448430 reaction equation
[CH2:1]([SH:3])[CH3:2].C(N(CC)CC)C.[F:11][C:12]([F:32])([F:31])[C:13]([N:15]([CH2:24][P:25]([O:29]Cl)([O:27]Cl)=[O:26])[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[O:14].[CH:33]([NH2:36])([CH3:35])[CH3:34]>O1CCCC1.CCOCC>[F:11][C:12]([F:32])([F:31])[C:13]([N:15]([CH:24]([NH:36][CH:33]([CH3:35])[CH3:34])[P:25]([OH:29])([O:27][S:3][CH2:1][CH3:2])=[O:26])[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[O:14]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 6363IsopropylamineHCID 8471TriethylamineHCID 53984889HCID 53984889, compound

Product 1

HCID 54120511HCID 54120511, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of ethanethiol (2.9 ml, 0.04 mole) and triethylamine (5.6 ml, 0.04 mole) in tetrahydrofuran (50 ml.) was added to n-butyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (14.3 g, 0.04 mole) in 250 ml. of ether at 0° C. After three hours, the solution was filtered and the filtrate was added to a cooled (0° C.) solution of isopropylamine (6.8 ml, 0.08 mole) in 50 ml. of tetrahydrofuran. After stirring for 16 hours at 25° C., the solution was filtered and the filtrate concentrated in vacuo. The residual oil was dissolved in 100 ml. methylene chloride and washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution. Concentration in vacuo afforded an oil which was chromatographed on silica gel eluting with ethyl acetate-cyclohexane (1:1) to afford n-butyl N-trifluoroacetyl-N-(isopropylamino(ethylthio)phosphonomethyl)glycinate (0.7 g) as a white solid, m.p. 64°-65° C.

Workup

  1. customat 0° C
  2. filtrationthe solution was filtered
  3. additionthe filtrate was added to
  4. filtrationthe solution was filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. dissolutionThe residual oil was dissolved in 100 ml
  7. washmethylene chloride and washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution
  8. concentrationConcentration in vacuo
  9. customafforded an oil which
  10. customwas chromatographed on silica gel eluting with ethyl acetate-cyclohexane (1:1)

Sources & evidence

ORD record
ord-9e60f9c77d5546feb5364747f9e9bb76
Source dataset
uspto-grants-1979_12
Patent number
US04180394

Reaction notes

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