Acetic Anhydride → HCID 20154106, compound

HRID 2413863Notes

Reaction equation

HRID 2413863 reaction equation
[NH2:1][C:2]1[C:11]2[S:10][CH2:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>ClCCCC>[C:12]([NH:1][C:2]1[C:11]2[S:10][CH2:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20154109HCID 20154109, compound

Product 1

HCID 20154106HCID 20154106, compound

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent2×

Procedure

To a solution of 21.1 g of 8-amino-2H-1-benzothiopyran in 200 ml of 1-chlorobutane was added a solution of 13.3 ml of acetic anhydride in 50 ml of 1-chlorobutane. The temperature of the mixture rose during the addition and the mixture was refluxed for an additional 30 minutes. The solution was cooled in ice and filtered to give 18.0 g of the desired acetamide as colorless needles, m.p. 133°-135° C. The mother liquor was concentrated to ~1/5 volume to give a second crop of 4.1 g, m.p. 133°-135° C.

Workup

  1. additionThe temperature of the mixture rose during the addition
  2. temperaturethe mixture was refluxed for an additional 30 minutes
  3. temperatureThe solution was cooled in ice
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e8b7a6febd1d4d5cab7a586adf147be3
Source dataset
uspto-grants-1988_01
Patent number
US04720298

Reaction notes

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