Chloroacetyl chloride → 2-chloro-N-(3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-4-yl)acetamid

HRID 343346Notes

Reaction equation

HRID 343346 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[S:12][CH:13]=[C:14]([CH3:15])[C:3]=12.[Cl:16][CH2:17][C:18](Cl)=[O:19]>>[Cl:16][CH2:17][C:18]([NH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[S:12][CH:13]=[C:14]([CH3:15])[C:3]=12)=[O:19]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 152251184-Amino-3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinoline

Product 1

HCID 538500202-chloro-N-(3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-4-yl)acetamid

Conditions

Temperature
25 °C

Procedure

To 12.7 g of 4-amino-3-methyl-5,6,7,8-tetrahydrothieno[2,3-b]quinoline, was added 40 ml of chloroacetyl chloride, and the mixture was refluxed for 40 minutes. The oil bath was removed and the reaction mixture was added with 50 ml of 1,2-dichloroethane and cooled to 25° C. The precipitated crystals were collected by filtration and washed with 1,2-dichloroethane. The crystals were suspended in a mixed solvent of 250 ml of chloroform, 55 ml of water and 60 ml of ethanol, and 4.3 ml of concentrated ammonia water was added thereto. The suspension was heated to 40° C. to dissolve substantially all the crystals.

Workup

  1. temperaturethe mixture was refluxed for 40 minutes
  2. customThe oil bath was removed
  3. additionthe reaction mixture was added with 50 ml of 1,2-dichloroethane
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with 1,2-dichloroethane
  6. additionwas added
  7. temperatureThe suspension was heated to 40° C.
  8. dissolutionto dissolve substantially all the crystals

Sources & evidence

ORD record
ord-2310f70dc66c4e979821b52a7f6ca394
Source dataset
uspto-grants-1999_01
Patent number
US05861411

Reaction notes

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