Hydrochloric Acid → HCID 19979808, compound

HRID 2051136Notes

Reaction equation

HRID 2051136 reaction equation
OO.[CH2:3]([SH:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:12][C:13]([NH2:15])=[S:14].[ClH:16]>C(O)C.C(OCC)C.O>[ClH:16].[CH2:3]([S:11][S:14][C:13](=[NH:12])[NH2:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 81441-OctanethiolHCID 2723790Thiourea

Product 1

HCID 19979808HCID 19979808, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Hydrogen peroxide (30% aqueous, 28.0 g) was added dropwise over 45 minutes to a stirred mixture of n-octanethiol (32.27 g, 0.221 mole), thiourea (20.1 g, 0.264 mole), concentrated hydrochloric acid (35 ml), water (35 ml) and ethanol (500 ml) maintained at 0°-10° C. After the addition was complete the reaction mixture was stirred at room temperature for 2 hours during which time a thick white precipitate formed. The mixture was filtered and the filtrate evaporated giving a solid residue. This was dissolved in ethanol (150 ml), diluted with diethyl ether (800 ml) and allowed to stand overnight at 0° C. Filtration gave white crystals of the product (46.3 g; 82%), melting point=77°-82° C.

Workup

  1. temperaturemaintained at 0°-10° C
  2. additionAfter the addition
  3. customformed
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated
  6. customgiving a solid residue
  7. waitto stand overnight at 0° C
  8. filtrationFiltration
  9. customgave white crystals of the product (46.3 g; 82%), melting point=77°-82° C.

Sources & evidence

ORD record
ord-abaf4969efc14eab8c4ceae79c4bac58
Source dataset
uspto-grants-1991_05
Patent number
US05017298

Reaction notes

Loading…