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

HRID 443888Notes

Reaction equation

HRID 443888 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-2b0f5d6f4f7c4cc99ae55f64419fc266
Source dataset
uspto-grants-1981_04
Patent number
US04262004

Reaction notes

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