Dimethylformamide → 3-((5-Nitrobenzothiazol-2-yl)amino)propanol

HRID 2417911Notes

Reaction equation

HRID 2417911 reaction equation
Cl[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].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[S:13][C:12]([NH:14][CH2:15][CH2:16][CH2:17][OH:18])=[N:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30187341-(2-Chloro-5-nitrophenyl)-3-(3-hydroxypropyl)thiourea

Product 1

HCID 30187353-((5-Nitrobenzothiazol-2-yl)amino)propanolYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21 parts of N-(2-chloro-5-nitrophenyl)-N'-(3-hydroxypropyl)thiourea, 10 parts of potassium carbonate and 180 parts of N,N-dimethylformamide is stirred and refluxed for 30 minutes. After cooling, 300 parts of water are added and the product is allowed to crystallize. It is filtered off and washed with water, yielding 13.3 parts (72.2%) of 3-[(5-nitro-2-benzothiazolyl)amino]-1-propanol; mp. 140°-144° C.

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureAfter cooling
  3. customto crystallize
  4. filtrationIt is filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-743183d9e5e54f24a5d59264d91e52a9
Source dataset
uspto-grants-1984_09
Patent number
US04471117

Reaction notes

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