Triphenylphosphine → HCID 54294130, compound

HRID 1085125Notes

Reaction equation

HRID 1085125 reaction equation
N(C([O:8][CH2:9][CH3:10])=O)=NC([O-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:30]1C=CC=[C:31]1CC(O)=O.OC[CH2:41][N:42]1[C:46]2[CH:47]=[CH:48][C:49]([O:51][C:52]([F:55])([F:54])[F:53])=[CH:50][C:45]=2[S:44][C:43]1=[N:56][C:57]([O:59][CH:60]=[CH2:61])=[O:58]>O1CCCC1.CO>[C:9]([S:30][CH2:31][CH2:41][N:42]1[C:46]2[CH:47]=[CH:48][C:49]([O:51][C:52]([F:54])([F:53])[F:55])=[CH:50][C:45]=2[S:44][C:43]1=[N:56][C:57]([O:59][CH:60]=[CH2:61])=[O:58])(=[O:8])[CH3:10]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 53913805HCID 53913805, compoundHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 54294130HCID 54294130, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-(2-Acetylthioethyl)-2-vinyloxycarbonylimino-6-trifluoromethoxybenzothiazoline may be obtained in the following manner: ethyl azodicarboxylate (10.5 cc) is added dropwise to triphenylphosphine (17.6 g) dissolved in tetrahydrofuran (150 cc) at 0° C. Stirring is continued for 30 minutes at this temperature. A solution of thiolacetic acid (4.8 cc) and 3-(2-hydroxyethyl)-2-vinyloxycarbonylimino-6-trifluoromethoxybenzothiazoline (11.7 g) in tetrahydrofuran (75 cc) is then added gradually. The reaction is continued for 1 hour at 0° C. and then 1 hour at a temperature in the region of 20° C. After concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa), the residue obtained is taken up in methanol (50 cc), then filtered and washed once with methanol (50 cc). 3-(2-Acetylthioethyl)-2-vinyloxycarbonylimino-6-trifluoromethoxybenzothiazoline (10.4 g), m.p. 173° C., is obtained.

Workup

  1. waitThe reaction is continued for 1 hour at 0° C.
  2. custom1 hour
  3. customin the region of 20° C
  4. concentrationAfter concentration to dryness under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customthe residue obtained
  6. filtrationfiltered
  7. washwashed once with methanol (50 cc)

Sources & evidence

ORD record
ord-ea97ec4cf1324322b2ba8030c13c4456
Source dataset
uspto-grants-1991_04
Patent number
US05008280

Reaction notes

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