Chloroacetyl chloride → HCID 23347799, compound

HRID 2163449Notes

Reaction equation

HRID 2163449 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:11])[CH2:8][CH2:9][CH2:10][C:3]1=2.C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>O1CCCC1>[Cl:19][CH2:20][C:21]([NH:11][CH:7]1[C:4]2[CH:5]=[CH:6][S:2][C:3]=2[CH2:10][CH2:9][CH2:8]1)=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 173886004,5,6,7-Tetrahydrobenzo[b]thiophen-4-amine hydrochloride

Product 1

HCID 23347799HCID 23347799, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 7.59 g of 4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine hydrochloride is stirred in 60 ml of dry tetrahydrofuran and 10.1 g of triethylamine in 20 ml of dry tetrahydrofuran is added. After stirring under a nitrogen atmosphere for 15 minutes, 3.5 ml or 5.25 g of chloroacetyl chloride in 30 ml of dry tetrahydrofuran is added dropwise, while the temperature is maintained at 30° C. to 40° C. After an hour of stirring, the mixture is filtered, the filter cake is washed with tetrahydrofuran, and the filtrate is evaporated to dryness. The residue is then triturated with water and the title compound, m.p. 115° C. to 119° C., is collected and washed with water and hexane.

Workup

  1. temperatureis maintained at 30° C. to 40° C
  2. stirringAfter an hour of stirring
  3. filtrationthe mixture is filtered
  4. washthe filter cake is washed with tetrahydrofuran
  5. customthe filtrate is evaporated to dryness
  6. customThe residue is then triturated with water
  7. customthe title compound, m.p. 115° C. to 119° C., is collected
  8. washwashed with water and hexane

Sources & evidence

ORD record
ord-db7c2d54884142d7badfc275e6e64581
Source dataset
uspto-grants-1979_01
Patent number
US04134899

Reaction notes

Loading…