Hydrochloric Acid → HCID 19900655, compound

HRID 1029524Notes

Reaction equation

HRID 1029524 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[NH:12]([C:14]([S:16][C:17]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:20]([OH:27])=[C:19]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:18]=1)=[S:15])[NH2:13].C(N(CC)C(C)C)(C)C.Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:31][C:28]([C:19]1[CH:18]=[C:17]([S:16][C:14]2[S:15][C:1](=[O:2])[NH:13][N:12]=2)[CH:22]=[C:21]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:20]=1[OH:27])([CH3:29])[CH3:30]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 54090446HCID 54090446, compound

Product 1

HCID 19900655HCID 19900655, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 12.5% solution of phosgene in toluene (8.6 mL, 9.6 mmol) is added dropwise to a -78° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl hydrazinecarbodithioate (1.5 g, 4.8 mmol) and N,N-diisopropylethylamine (3.3 mL, 19.2 mmol) in tetrahydrofuran (150 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and water. The pH of the aqueous phase is adjusted to 3 with 1N hydrochloric acid. The organic phase is washed twice with water, then with a saturated solution of sodium bicarbonate followed by brine. Drying over magnesium sulfate and evaporation of the solvents gives a solid which is crystallized twice from isopropyl ether/hexane to afford 0.7 g (43%) of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]thio]-1,3,4-thiadiazol-2(3H)-one, mp 194°-197° C. (dec).

Workup

  1. additionthen poured into a separatory funnel
  2. washThe organic phase is washed twice with water
  3. dry with materialDrying over magnesium sulfate and evaporation of the solvents
  4. customgives a solid which
  5. customis crystallized twice from isopropyl ether/hexane

Sources & evidence

ORD record
ord-6841a7d6751948dd9ec5cf311eaa65cd
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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