Ethanol → HCID 13178725, compound

HRID 904769Notes

Reaction equation

HRID 904769 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][Cl:7])([O-:3])=[O:2].[NH2:12][C:13]([NH2:15])=[S:14].C(O)C>ClCCCC>[ClH:7].[C:13]([S:14][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])(=[NH:12])[NH2:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 119212-Nitrobenzyl chlorideHCID 2723790Thiourea

Product 1

HCID 13178725HCID 13178725, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Procedure

A solution of 153.9 g of o-nitrobenzylchloride and 68.5 g of thiourea in 900 ml of #2B ethanol was stirred at reflux temperature (80°) for 11/4 hours. The solution was cooled to 60° and 1.1 liters of 1-chlorobutane was added. Further cooling to 15° produced a heavy precipitate. The precipitate was filtered, washed with 1-chlorobutane and dried to yield 185.9 g of 2-nitrophenylmethyl carbamimidothioate hydrochloride, m.p. 190°-192°.

Workup

  1. temperatureat reflux temperature (80°) for 11/4 hours
  2. temperatureThe solution was cooled to 60°
  3. temperatureFurther cooling to 15°
  4. customproduced a heavy precipitate
  5. filtrationThe precipitate was filtered
  6. washwashed with 1-chlorobutane
  7. customdried

Sources & evidence

ORD record
ord-fa117951de434a1886ea9dbe517c11e4
Source dataset
uspto-grants-1983_12
Patent number
US04420325

Reaction notes

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