Sulfuric Acid → HCID 20349865, compound

HRID 1449124Notes

Reaction equation

HRID 1449124 reaction equation
N([O-])=O.[Na+].OS(O)(=O)=O.[NH2:10][C:11]1[S:12][C:13]2[CH:19]=[C:18]([S:20][C:21]#[N:22])[CH:17]=[CH:16][C:14]=2[N:15]=1.[CH3:23][C:24]1[CH:36]=[CH:35][C:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:33][C:25]=1[NH:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C([O-])(=O)C.[NH4+:46]>O>[S:20]([C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:11]([N:10]=[N:46][C:35]3[C:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:33][C:25]([NH:26][CH:27]4[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]4)=[C:24]([CH3:23])[CH:36]=3)[S:12][C:13]=2[CH:19]=1)[C:21]#[N:22]

Participants

7

Reactant 5

HCID 1118Sulfuric Acid2×HCID 816002-Amino-6-thiocyanato-1,3-benzothiazoleHCID 517165Ammonium AcetateHCID 20349866HCID 20349866, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20349865HCID 20349865, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium nitrite (0.76 g.) is added portionwise to 5 ml. of conc. H2SO4. This solution is cooled in an ice bath and 10 ml. 1:5 acid is added, keeping the temperature below 15° C. This mixture is stirred at 0° to 5° C. and 2.07 g. of 2-amino-6-thiocyanatobenzothiazole is added, followed by 10 ml. of 1:5 acid. The diazotization is stirred at 0° to 5° C. for 2.0 hr. and is then added to a solution of 2.82 g. 2-methyl-5-methylsulfonamido-N-cyclohexylaniline in a mixture of 50 ml. 15% H2SO4 and 50 ml. of 1:5 acid. The coupling is buffered with solid ammonium acetate and allowed to react at about 5° C. for 2.0 hr. After drowning in water, the product is collected by filtration, washed with water, and dried in air. This azo compound, 4-(6-thiocyanato-2-benzothiazolylazo)-2-methyl-5-methylsulfonamido-N-cyclohexylaniline, gives fast red dyeings on polyester fibers.

Workup

  1. temperatureThis solution is cooled in an ice bath
  2. addition1:5 acid is added
  3. customthe temperature below 15° C
  4. stirringThe diazotization is stirred at 0° to 5° C. for 2.0 hr
  5. additionand is then added to a solution of 2.82 g
  6. customto react at about 5° C. for 2.0 hr
  7. filtrationthe product is collected by filtration
  8. washwashed with water
  9. customdried in air

Sources & evidence

ORD record
ord-92c50bf5da2b4d1fbdfa025df5e461d3
Source dataset
uspto-grants-1980_02
Patent number
US04189428

Reaction notes

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