3-Amino-1-propanol → 1-(2-Chloro-5-nitrophenyl)-3-(3-hydroxypropyl)thiourea

HRID 2417910Notes

Reaction equation

HRID 2417910 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]=[C:12]=[S:13].[NH2:14][CH2:15][CH2:16][CH2:17][OH:18]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][OH:18])=[S:13]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 926811-Chloro-2-isothiocyanato-4-nitrobenzene

Product 1

HCID 30187341-(2-Chloro-5-nitrophenyl)-3-(3-hydroxypropyl)thioureaYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 24 parts of 1-chloro-2-isothiocyanato-4-nitrobenzene in 200 parts of ethanol 95% are added dropwise 9 parts of 3-amino-1-propanol at a temperature below 20° C. Upon completion, stirring is continued for 30 minutes at room temperature. The reaction mixture is evaporated. The residue is crystallized from acetonitrile. The product is filtered off and dried, yielding 23 parts (72%) of N-(2-chloro-5-nitrophenyl)-N'-(3-hydroxypropyl)thiourea; mp. 126.8° C.

Workup

  1. customThe reaction mixture is evaporated
  2. customThe residue is crystallized from acetonitrile
  3. filtrationThe product is filtered off
  4. customdried

Sources & evidence

ORD record
ord-b508b8a7443b4001aa8c6558af803e13
Source dataset
uspto-grants-1984_09
Patent number
US04471117

Reaction notes

Loading…