Dichloromethane → HCID 16222599, compound

HRID 2250467Notes

Reaction equation

HRID 2250467 reaction equation
Cl[C:2]1[CH:6]=[CH:5]S[C:3]=1[C:7]([NH:9]N)=O.[NH2:11][NH2:12].[Cl:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19](Cl)=[O:20].[CH2:22](Cl)Cl>>[Cl:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]1[O:20][C:22]([N:9]2[CH2:5][CH2:6][CH2:2][CH2:3][CH2:7]2)=[N:12][N:11]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 9321HydrazineHCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 23570764HCID 23570764, compound

Product 1

HCID 16222599HCID 16222599, compoundYield 82%

Conditions

Temperature
0 °C

Procedure

3-Chlorothiophene-2-carboxylic acid hydrazide. To a solution of hydrazine (0.860 mL, 27.6 mmol) at 0° C. was added a clear solution of 3-chlorothiophene-2-carbonyl chloride (1.00 g, 5.52 mmol) and CH2Cl2 (11.0 mL). The reaction was stirred at 0° C. for 0.5 h and then equilibrated to room temperature. The solvent was evaporated and the yellow solid was diluted with ethyl acetate (70 mL), washed with water (2×20 mL), dried over MgSO4, filtered and concentrated to give 0.80 g (82%) of the title compound as a white solid. 1H NMR (CDCl3): 9.41 (s, 1H), 7.81 (d, 1H, J=5.2 Hz), 7.13 (d, 1H, J=5.5 Hz), 4.57 (s, 2H).

Workup

  1. customequilibrated to room temperature
  2. customThe solvent was evaporated
  3. additionthe yellow solid was diluted with ethyl acetate (70 mL)
  4. washwashed with water (2×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0251ec2ab84344048d881688bda01085
Source dataset
uspto-grants-2008_01
Patent number
US07317029B2

Reaction notes

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