p-Chlorothiophenol → HCID 86736748, compound

HRID 1448431Notes

Reaction equation

HRID 1448431 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]([CH2:14][P:15]([O:19]Cl)([O:17]Cl)=[O:16])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=[O:4].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(N(CC)CC)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][CH:38]=1>CCOCC>[F:1][C:2]([F:22])([F:21])[C:3]([N:5]([CH:14]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[P:15]([OH:19])([O:17][S:43][C:40]1[CH:41]=[CH:42][C:37]([Cl:36])=[CH:38][CH:39]=1)=[O:16])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 7815p-ChlorothiophenolHCID 8083MorpholineHCID 8471Triethylamine2×HCID 53984889HCID 53984889, compound

Product 1

HCID 86736748HCID 86736748, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of n-butyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (14.3 g, 0.04 mole) in 250 ml. of ether was added slowly to a solution of morpholine (3.5 ml, 0.04 mole) and triethylamine (5.6 ml, 0.04 mole) in 100 ml. of ether. After three hours, the solution was filtered and the filtrate was added slowly to a cooled (0° C.) solution of p-chlorothiophenol (5.7 g, 0.04 mole) and triethylamine (5.6 ml, 0.04 mole) in 100 ml. of ether. After 16 hours at 25° C., the solution was filtered and the filtrate was concentrated in vacuo and the residual semi-solid was crystallized from ethyl acetate/cyclohexane (1/10). Recrystallization from hexane yielded butyl N-trifluoroacetyl-N-(morpholino(p-chlorothiophenoxy)phosphonomethyl)glycinate (2.1 g) as a white solid, m.p. 79.5°-81° C.

Workup

  1. filtrationthe solution was filtered
  2. additionthe filtrate was added slowly to
  3. waitAfter 16 hours at 25° C.
  4. filtrationthe solution was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residual semi-solid was crystallized from ethyl acetate/cyclohexane (1/10)
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-0e6ccdce605e49a7bc4627e95476e809
Source dataset
uspto-grants-1979_12
Patent number
US04180394

Reaction notes

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