Hydrochloric Acid → HCID 178479082, compound

HRID 544182Notes

Reaction equation

HRID 544182 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, to which 300 ml of concentrated hydrochloric acid was added while stirring at room temperature. They were reacted at room temperature for 3 hours and then cooled with ice to precipitate crystals. These crystals were collected and washed with acetone to obtain 110 g of 1-(3-aminophenyl)-5-mercaptotetrazole hydrochloride. This amine hydrochloride was dispersed in 750 ml of acetonitrile, and after addition of 485 ml of triethylamine, 125 g of butyl isocyanate was added dropwise at room temperature. They were reacted at room temperature for 6 hours. At the end of the time, 2,200 ml of water was added, and the resulting mixture was adjusted to pH 2 by the addition of hydrochloric acid. The thus-precipitated crystals were collected and recrystallized from ethanol to obtain 69 g (yield: 46%) of the desired product, m.p. 171°-172° C. (decomposition).

Workup

  1. customThey were reacted at room temperature for 3 hours
  2. temperaturecooled with ice
  3. customto precipitate crystals
  4. customThese crystals were collected
  5. washwashed with acetone

Sources & evidence

ORD record
ord-1ea284b1557242838a0e53ff87de5c60
Source dataset
uspto-grants-1984_05
Patent number
US04448878

Reaction notes

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