Hydrochloric Acid → HCID 779038, compound

HRID 1186636Notes

Reaction equation

HRID 1186636 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.N1C=CC=CC=1.Cl>ClCCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7242O-ToluidineHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 779038HCID 779038, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(RK1-1-22) I A solution of 4-nitrobenzenesulfonyl chloride (200 mg, 0.90 mmol), o-toluidine (106 mg, 0.99 mmol), and pyridine (79 mg, 0.08 ml, 0.993 mmol) in 5.0 mL 1,2-dichloroethane was heated to 150° C. for 10 minutes in the microwave. A 1M HCl solution was added until the pH of the mixture indicated pH=2, and the acidified aqueous layer was separated and extracted with CH2Cl2 (3×10 mL). The combined organic fractions were washed successively with brine and water then dried over Na2SO4 and evaporated to dryness to afford the title compound as a peach solid (127 mg, 47%). Mp=139-142° C. (lit. 157-159° C., Tetrahedron 62(25), 6100-6106; 2006); 1H NMR (400 MHz, CDCl3) δ 8.28 (d, J=9.0 Hz, 2H), 7.89 (d, J=9.0 Hz, 2H), 7.28-7.27 (m, 1H), 7.20-7.12 (m, 3H), 6.30 (br s, 1H), 2.01 (s, 3H).

Workup

  1. customthe acidified aqueous layer was separated
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. washThe combined organic fractions were washed successively with brine and water
  4. dry with materialthen dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-c71b5fe785d64f58a8bb7e83614286ed
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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