Dimethylformamide → 2-[(5-Nitro-1,3-benzothiazol-2(3H)-ylidene)amino]ethan-1-ol

HRID 1902625Notes

Reaction equation

HRID 1902625 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][OH:17])=[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][OH:17])=[N:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3018768N-(2-Chloro-5-nitrophenyl)-N'-(2-hydroxyethyl)carbamimidothioic acid

Product 1

HCID 30187692-[(5-Nitro-1,3-benzothiazol-2(3H)-ylidene)amino]ethan-1-olYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 28 parts of N-(2-chloro-5-nitrophenyl)-N'-(2-hydroxyethyl)thiourea, 14.5 parts of potassium carbonate and 225 parts of N,N-dimethylformamide is stirred and refluxed for one hour. After cooling, 300 parts of water are added. The precipitated product is filtered off, washed with water and dried, yielding 20.5 parts (82%) of 2-[(5-nitro-2-benzothiazolyl)amino]ethanol; mp. 183.4° C.

Workup

  1. temperaturerefluxed for one hour
  2. temperatureAfter cooling
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fbd968128ff04f6180ef718f492c5fb6
Source dataset
uspto-grants-1982_12
Patent number
US04364942

Reaction notes

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