2-Nitrobenzyl chloride → HCID 13178725, compound

HRID 434458Notes

Reaction equation

HRID 434458 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]>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

4

Reactant 2

HCID 119212-Nitrobenzyl chlorideHCID 2723790Thiourea

Product 1

HCID 13178725HCID 13178725, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Procedure

A solution of 34.3 g of o-nitrobenzyl chloride and 15.2 g of thiourea in 250 ml of #2B alcohol was refluxed for 11/2 hours. The solution was cooled to 60° and 250 ml of 1-chlorobutane added. Further cooling to 20° yielded a precipitate which was filtered, washed with 1-chlorobutane and dried at 65° to give 38.1 g of 2-nitrophenylmethyl carbamimidothioate hydrochloride, m.p. 190°-192°.

Workup

  1. temperatureThe solution was cooled to 60°
  2. temperatureFurther cooling to 20°
  3. customyielded a precipitate which
  4. filtrationwas filtered
  5. washwashed with 1-chlorobutane
  6. customdried at 65°

Sources & evidence

ORD record
ord-fabdfe8ceaba46e9ac76050c30f2c125
Source dataset
uspto-grants-1983_08
Patent number
US04397679

Reaction notes

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