Thiourea → HCID 17754665, compound

HRID 1706704Notes

Reaction equation

HRID 1706704 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[Cl:10].[NH2:11][C:12]([NH2:14])=[S:13]>C(O)C>[Cl:10][C:4]1[C:5]([Cl:9])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][S:13][C:12](=[NH:11])[NH2:14]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 27346021-(Bromomethyl)-2,3-dichlorobenzene

Product 1

HCID 17754665HCID 17754665, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-Dichlorotoluene (8.05 g., 0.05 mol.) dissolved in 150 ml. of carbon tetrachloride containing N-bromosuccinimide (8.9 g., 0.05 mol.) was heated to reflux and irradiated with a 275-watt sunlamp for two hours. The mixture was cooled, filtered and evaporated to give α-bromo-2,3-dichlorotoluene. The α-bromo-2,3-dichlorotoluene (2.4 g., 0.01 mol.) and thiourea (0.38 g., 0.005 mol.) were dissolved in 25 ml. of ethanol and refluxed for about sixteen hours. The mixture was cooled, concentrated, treated with ether, filtered and the filter cake recrystallized from water to give carbamimidothioic acid 2,3-dichlorobenzyl ester, m.p. 238°-243° C. (dec.).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. additiontreated with ether
  4. filtrationfiltered
  5. customthe filter cake recrystallized from water

Sources & evidence

ORD record
ord-575c5703cd924557a7c4a510740e4502
Source dataset
uspto-grants-1980_06
Patent number
US04208430

Reaction notes

Loading…