Hydrochloric Acid → HCID 178479082, compound

HRID 1979600Notes

Reaction equation

HRID 1979600 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([N:15]2[C:19]([SH:20])=[N:18][N:17]=[N:16]2)[CH:12]=[CH:13][CH:14]=1)(=O)CCCCC.[ClH:21]>C(O)C>[ClH:21].[NH2:8][C:9]1[CH:10]=[C:11]([N:15]2[C:19]([SH:20])=[N:18][N:17]=[N:16]2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178445140HCID 178445140, compound

Product 1

HCID 178479082HCID 178479082, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 450 ml of ethanol was dispersed 150 g (0.51 mol) of 1-(3-hexaneamidophenyl)-5-mercaptotetrazole, and 300 ml of concentrated hydrochloric acid was added to the resulting dispersion while stirring at room temperature. They were further reacted at room temperature for 3 hours and, thereafter, cooled with ice. The thus-precipitated crystals were filtered off and washed with acetone to obtain 110 g of a 1-(3-aminophenyl)-5-mercaptotetrazole hydrochloric acid salt. This amine hydrochloric acid salt was dispersed in 750 ml of acetonitrile, and 485 ml of triethylamine was added thereto. Thereafter, 125 g of butyl isocyanate was added dropwise at room temperature. They were further reacted at room temperature for 6 hours. At the end of the time, 2,200 ml of water was added, and the pH of the resulting solution was adjusted to 2 with hydrochloric acid. The thus-precipitated crystals were filtered off, and recrystallized from ethanol to obtain 69 g (yield, 46%) of the desired compound, m.p. 171°-172° C. (decomposition).

Workup

  1. additionwas added to the resulting dispersion
  2. customThey were further reacted at room temperature for 3 hours
  3. temperaturecooled with ice
  4. filtrationThe thus-precipitated crystals were filtered off
  5. washwashed with acetone

Sources & evidence

ORD record
ord-2b5c1b7a660548a0b0bd6239a4bea36a
Source dataset
uspto-grants-1984_11
Patent number
US04481290

Reaction notes

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