Chloride → HCID 13084266, compound

HRID 1164321Notes

Reaction equation

HRID 1164321 reaction equation
[O:1]=[C:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[N:3]1[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].S(Cl)([Cl:23])(=O)=O.[Cl-]>C(O)(=O)C>[Cl:23][C:7]1[C:8]2[C:9]3[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2](=[O:1])[C:10]=3[CH:11]=[CH:12][CH:13]=2

Participants

5

Reactant 3

HCID 312ChlorideHCID 24648Sulfuryl chlorideHCID 13084265HCID 13084265, compound

Product 1

HCID 13084266HCID 13084266, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 2-oxo-benz[cd]indole-1(2H)acetic acid, ethyl ester (17 g, 0.067 mole, described in Example 3) in glacial acetic acid (67 mL) was added sulfuryl chloride (9 g, 5.4 ml, 0.067 mol) dropwise at room temperature over a period of 50 min with mechanical stirring. The solid initially disappeared after a few milliliters of the chloride were added. Towards the end of additon, the product started to precipitate. The reaction mixture was stirred at room temperature for an additional 30 min and then at 94° C. for 2 hr. After cooling to room temperature the mixture was poured into water (200 mL). The precipitate was filtered, dried (18.3 g), and crystallized from boiling ethanol (360 mL) to give the title compound: mp 138°-140° C.; Anal. Calcd for C15H12ClNO3 : C, 62.19% H, 4.18% N, 4.83% and Found: C, 61.98% H, 4.08% N, 4.82%; IR (CHCl3) 1745 and 1710 cm-1 ; UV max (methanol) 339 (ε3690), 322 (2530), 279 (6030), 258 (18,680) and 214 nm (32,760); NMR (CDCl3)δ 1.25 (t, 3H), 4.2 (q, 2H), 4.65 (s, 2H), and 7.5 (m, 5H).

Workup

  1. additionwere added
  2. customto precipitate
  3. waitat 94° C. for 2 hr
  4. temperatureAfter cooling to room temperature the mixture
  5. additionwas poured into water (200 mL)
  6. filtrationThe precipitate was filtered
  7. customdried (18.3 g)
  8. customcrystallized

Sources & evidence

ORD record
ord-0aaf65d84b3c4c809dd451ce169e23ab
Source dataset
uspto-grants-1983_01
Patent number
US04369188

Reaction notes

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