N,N-Dimethylaniline → HCID 178433864, compound

HRID 46422

Reaction equation

HRID 46422 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.[OH:11][C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=[C:14]([CH3:23])[C:13]=1[N:24]=[N:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.CN(C)C1C=CC=CC=1.O>O1CCCC1>[NH:6]1[C:5]2[CH:9]=[CH:10][C:2]([NH:1][C:30](=[O:31])[C:29]3[CH:33]=[CH:34][C:26]([N:25]=[N:24][C:13]4[C:14]([CH3:23])=[N:15][N:16]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:12]=4[OH:11])=[CH:27][CH:28]=3)=[CH:3][C:4]=2[N:8]=[N:7]1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 178433863HCID 178433863, compoundHCID 178507366HCID 178507366, compound

Product 1

HCID 178433864HCID 178433864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-aminobenzotriazole (0.78 g), 4-(5-hydroxy-3-methyl-1-phenylpyrazol-4-ylazo)benzoyl chloride (2.0 g) and N,N-dimethylaniline (0.71 g) in dry tetrahydrofuran (15 ml) was stirred overnight and water (50 ml) was added. The precipitate was filtered and crystallized in aqueous pyridine (1.9 g), m.p. 285° decomp., λmax (methanol)=396 nm.

Workup

  1. filtrationThe precipitate was filtered
  2. customcrystallized in aqueous pyridine (1.9 g)

Sources & evidence

ORD record
ord-861923de7ac74a1f8d42779d1685c841
Source dataset
uspto-grants-1979_11
Patent number
US04173478

Linked notes

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